Isoxazoline-substituted benzamide compound and pesticide

ABSTRACT

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: 
     
       
         
         
             
             
         
       
     
     wherein A 1 , A 2  and A 3  independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., X is halogen atom, C 1 -C 6 haloalkyl, etc., Y is halogen atm, C 1 -C 6 alkyl, etc., R 1  is C 1 -C 12 alkyl arbitrarily substituted with R 16 , C 3 -C 12 alkenyl, arbitrarily substituted with R 16  is oxygen atom or sulfur atom, —N(R 20 )R 19 , etc., R 2  is hydrogen atom, C 1 -C 4 alkoxy C 1 -C 6 alkyl, etc., R 3  is C 1 -C 6 haloalkyl, etc., R 16  is halogen atom, cyano, phenyl substituted with (Z) p1 , D-1 to D-60, E-1 to E-49, etc., R 19  is phenyl, phenyl substituted with (Z) p1 , etc., R 20  is hydrogen atom, C 1 -C 6 alkyl, etc., Z is halogen atom, nitro, C 1 -C 4 alkoxy, etc., D-1 to D-60 are 5- or 6-membered aromatic heterocyclic rings, E-1 to E-49 are 5- or 6-membered saturated heterocyclic rings, m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.

This is a Division of application Ser. No. 11/514,921, filed Sep. 5, 2006, which in turn is a National Stage of Application No. PCT/JP05/04268, filed, Mar. 4, 2005, which claims priority to Japanese Patent Applications Nos. 2004-200119, filed Jul. 7, 2004, and 2004-061749, filed Mar. 5, 2004. The disclosure of the prior applications are hereby incorporated by reference herein in their entirety.

TECHNICAL FIELD

The present invention relates to a novel isoxazoline-substituted benzamide compound and the salt thereof, and a pesticide characterized by containing the compound as an active ingredient. The pesticide in the present invention means a pest controlling agent applied for harmful arthropods in agricultural and horticultural field or livestock farming and hygienic field (endo-parasiticides and ecto-parasiticides for mammals or birds as domestic animals or pets, or hygienic pest- or unpleasant pest-controlling agents for domestic or business use). In addition, agricultural chemicals in the present invention mean insecticides, acaricides (miticides), nematicides, herbicides and fungicides, and the like.

BACKGROUND ART

Conventionally, as to isoxazoline-substituted benzoic acid amide compounds, the followings are known: a report of synthesis by use of solid phase synthesis of 4-(5-methyl-5-substituted pyrrolyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives (see, Non-patent Document 1); 4-(5-pyridyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives have matrix metalloprotease and TNF-α inhibition activity, or the like, and can be used as an anti-inflammatory agent or a chondro-protective agent (see, Patent Document 1); 4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives, 3-(5-substituted carbamoylmethyl-5-substituted alkyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives and 4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzamidine derivatives have platelet glycoprotein IIb/IIIa fibrinogen receptor complex competitive activity or factor Xa inhibition activity or the like, and can be used as a thrombolysis agent or a therapeutic agent of thronbo-embolic disorder (see, for example Patent Documents 2-5), etc. In addition, it is known that other specific substituted isoxazoline compound can be used as a production intermediate of HIV protease inhibitors, or production intermediate of insecticides (see, for example Patent Documents 6 and 7). However, there is no disclosure on 4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazole-3-yl)benzoic acid amide compounds according to the present invention, and further the usefulness thereof as a pesticide is not known at all.

On the other hand, as to 3-(4-substituted phenyl)-4,5-dihydroisoxazole derivatives, 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 7), 3-alkoxyphenyl-5-substituted-5-phenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 8), 3-alkoxyphenyl-5-substituted alkyl-5-substituted carbamoyl-4,5-dihydroisoxazole derivatives (see, Patent Document 9), 3-(4-halophenyl)-5-substituted-5-substituted phenyl-4,5-dihydroisoxazole derivatives (see, Patent Documents 10 and Non-patent Document 2), and 3-(4-nitrophenyl)-5-substituted-5-substituted phenyl-4,5-dihydroisoxazole derivatives (see, patent Document 11 and Non-patent Document 3), etc. are known. However, 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.

Further, as to 4-hydroxyiminomethyl benzoic acid amide derivatives, 4-hydroxyiminomethyl-N,N-dimethyl benzoic acid amide (see, Non-patent Document 4), 4-hydroxyiminomethyl benzoyl piperidine derivatives (see, Patent Documents 12 and 13), 4-hydroxyiminomethyl-N-bicycloalkyl benzoic acid amide derivatives (see, Patent Document 14), and 6-(hydroxyiminomethyl)pyridine-2-carboxamide derivatives (see, Non-patent Document 5), etc. are known. However, 4-hydroxyiminomethyl benzoic acid amide derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.

In addition, as to haloalkenylbenzene derivatives, substituted 3,3,3-trifluoro-2-propenylbenzene derivatives (see, Non-patent Documents 6-8), etc. are known. However, specific substituted haloalkenylbenzene derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.

Patent Document 1: WO 01/070673 Pamphlet

Patent Document 2: WO 96/038426 Pamphlet

Patent Document 3: WO 97/023212 Pamphlet

Patent Document 4: WO 95/014683 Pamphlet

Patent Document 5: WO 97/048395 Pamphlet

Patent Document 6: WO 99/014210 Pamphlet

Patent Document 7: WO 04/018410 Pamphlet

Patent Document 8: WO 95/024398 Pamphlet

Patent Document 9: WO 98/057937 Pamphlet

Patent Document 10: EP 0455052 A1 (1991)

Patent Document 11: WO 2004/018410 Pamphlet

Patent Document 12: WO 95/019773 Pamphlet

Patent Document 13: WO 00/066558 Pamphlet

Patent Document 14: WO 97/000853 Pamphlet

Non-patent Document 1: J. Comb. Chem., vol. 6, p. 142 (2004)

Non-patent Document 2: Synth. Commun., vol. 33, p. 4163 (2003)

Non-patent Document 3: Australian J. Chem., vol. 32, p. 1487 (1979)

Non-patent Document 4: J. Chem. Soc. Perkin Trans, 1, p. 643 (1979)

Non-patent Document 5: J. Org. Chem., vol. 35, p. 841 (1970)

Non-patent Document 6: J. Org. Chem., vol. 24, p. 238 (1959)

Non-patent Document 7: J. Am. Chem. Soc., vol. 101, p. 357 (1979)

Non-patent Document 8: Bull. Chem. Soc. Jpn., vol. 69, p. 3273 (1996)

DISCLOSURE OF INVENTION Problems to be Solved by the Invention

Recently, pests acquire resistance by the use of pesticides such as insecticides or fungicides over long term, and thus control by the insecticides or fungicides that have been conventionally used becomes difficult. In addition, a part of known pesticides has a high toxicity, or some of them start to disturb native ecosystems due to long-term persistency. Under the circumstances, it is expected all the time to develop a novel pesticide having a low toxicity and a low persistency.

Means for Solving the Problems

The inventors have eagerly investigated in order to solve the above-mentioned problems, and as a result of it, they found that novel isoxazoline-substituted benzamide compounds of formula (I) are extremely useful compounds having excellent pest controlling activity, particularly insecticidal activity and acaricidal activity, and having little adverse affect on non-targeted beings such as mammals, fishes and useful insects, etc. Thus, the present invention has been accomplished.

That is, the present invention relates to the following aspects (1) to (15):

(1) An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:

wherein A¹, A² and A³ independently of one another are carbon atom or nitrogen atom,

G is benzene ring, nitrogen-containing 6-membered aromatic heterocyclic ring, furan ring, thiophene ring, or 5-membered aromatic heterocyclic ring containing two or more hetero atoms selected from oxygen atom, sulfur atom and nitrogen atom,

W is oxygen atom or sulfur atom,

X is halogen atom, cyano, nitro, azido, —SCN, —SF₅, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R⁴, C₂-C₆alkenyl, C₂-C₆alkenyl arbitrarily substituted with R⁴, C₃-C₈cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₆alkynyl, C₂-C₆alkynyl arbitrarily substituted with R⁴, —OH,

—OR⁵, —OSO₂R⁵, —SH, —S(O)_(r)R⁵, —N═CHOR⁸, —N═C(R⁹)OR⁸, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)=NOR¹¹, —S(O)₂OR⁹, —S(O)₂NHR¹⁰, —S(O)₂N(R¹⁰)R⁹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49, when m is 2, 3, 4 or 5, each X may be identical with or different from each other,

further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂N(R¹⁵)—, —CH₂N(R¹⁵)CH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —CH₂CH═CH—, —OCH═CH—, —SCH═CH—, —N(R¹⁵)CH═CH—, —OCH═N—, —SCH═N—, —N(R¹⁵)CH═N—, —N(R¹⁵)N═CH—, —CH═CHCH═CH—, —OCH₂CH═CH—, —N═CHCH═CH—, —N═CHCH═N— or —N═CHN═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other,

Y is halogen atom, cyano, nitro, azido, —SCN, —SF₅, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R⁴, C₂-C₆alkynyl, C₂-C₆alkynyl arbitrarily substituted with R⁴, —OH, —OR⁵, —OSO₂R⁵, —SH, —S(O)R⁵, —NHR⁷, —N(R⁷)R⁶, —N═CHOR⁸, —N═C(R⁹)OR⁸, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49, when n is 2, 3 or 4, each Y may be identical with or different from each other,

further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-membered ring together with carbon atoms to which the two Ys are bonded by forming —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —SCH₂CH₂S—, —OCH═N— or —SCH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other, R¹ and R² independently of each other are hydrogen atom, cyano, C₁-C₁₂alkyl, C₁-C₁₂alkyl arbitrarily substituted with R¹⁶, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl arbitrarily substituted with R¹⁶, C₂-C₁₂alkenyl, C₂-C₁₂alkenyl arbitrarily substituted with R¹⁶, C₃-C₁₂cycloalkenyl, C₃-C₁₂halocycloalkenyl, C₃-C₁₂alkynyl, C₃-C₁₂alkynyl arbitrarily substituted with R¹⁶, —SR⁹, —S(O)₂R⁹, —SN(R¹⁸)R¹⁷, —S(O)₂N(R¹⁰)R⁹, —OR¹⁹, —N(R²⁰)R¹⁹, N═CHR^(19b), —N═C(R^(19b))R^(19a), —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)N(R¹⁰)R⁹, —C(═NR¹¹)OR⁹, —C(═NR¹¹)SR⁹, —C(═NR¹¹)N(R¹⁰)R⁹, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-63, D-65, E-3 to E-9, E17, E-23 to E-31, E-33, E-34 or E-45, or R¹ and R² together form ═C(R^(2a))R^(1a), or R¹ and R² together may form 3- to 8-membered ring together with the nitrogen atom bonding them by forming C₂-C₇ alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy (C₁-C₆)alkyl, C₁-C₆alkoxy, formyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl, C₁-C₆haloalkylaminocarbonyl, phenyl, phenyl substituted with (Z)_(p1), D-47, D-50, D-51, D-53 or 54,

or in case where substituent Y is present at the adjacent position, R² together with Y may form 5- or 6-membered ring together with the atom bonding them by forming —CH₂—, —CH₂CH₂—, —CH₂O—, —CH₂S—, —CH₂N(R⁶)—, —CH═CH— or —CH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylidene, C₁-C₆haloalkylidene, oxo or thioxo,

R^(1a) and R^(2a) together may form 5- or 6-membered ring together with the carbon atom bonding them by forming C₄-C₅ alkylene chain or C₄-C₅ alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms, sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio or C₁-C₆haloalkylthio,

R³ is halogen atom, cyano, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R⁴, C₃-C₆alkenyl, C₂-C₆alkenyl arbitrarily substituted with R⁴, C₃-C₆alkynyl, C₂-C₆alkynyl arbitrarily substituted with R⁴, —OR⁵, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹,

—CH═NOR¹¹, —C(R⁹)=NOR¹¹, —Si(R¹³)(R¹⁴)R¹², —P(O)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,

D-1 to D-65 are aromatic heterocyclic rings of the following formulae, respectively

Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl, C₁-C₄haloalkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —NH₂, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, —C(O)NH₂, C₁-C₆alkylaminocarbonyl, C₁-C₆haloalkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl, —C(S)NH₂, —S(O)₂NH₂, C₁-C₆alkylaminosulfonyl, di(C₁-C₆alkyl)aminosulfonyl, phenyl or phenyl arbitrarily substituted with halogen atom, when p1, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other,

further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or 6-membered ring together with carbon atoms to which the two Zs are bonded by forming —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —CH₂CH₂CH₂S—, —OCH₂CH₂S— or —CH═CH—CH═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄alkylthio,

E-1 to E-49 are saturated heterocyclic rings of the following formulae, respectively

R⁴ is halogen atom, cyano, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, —OH, —OR⁵, —SH, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —N(R¹⁰)CHO, —N(R¹⁰)C(O)R⁹, —N(R¹⁰)C(O)OR⁹, —N(R¹⁰)C(O)SR⁹,

—N(R¹⁰)C(S)OR⁹, —N(R¹⁰)C(S)SR⁹, —N(R¹⁰)S(O)₂R⁹, —C(O)OR⁹, —C(O)N(R¹⁰)R⁹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49, R⁵ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R²⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R²⁴, C₂-C₆alkenyl, C₂-C₆alkenyl arbitrarily substituted with R²⁴, C₃-C₈cycloalkenyl, C₃-C₈halocycloalkenyl, C₃-C₆alkynyl, C₃-C₆alkynyl arbitrarily substituted with R²⁴, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, D-62, D-63, D-65, E-3 to E-9, E-23 to E-31, E-34 or E-45,

R⁶ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R²⁴, C₃-C₆cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —OH, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, phenylthio, phenylthio substituted with (Z)_(p1),

—SN(R¹⁸)R¹⁷, —S(O)₂R⁹, —S(O)₂N(R¹⁰)R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —C(O)C(O)R⁹, —C(O)C(O)OR⁹, —P(O)(OR²¹)₂ or —P(S)(OR²¹)₂,

R⁷ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄ alkylthio C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl or C₁-C₆alkoxycarbonyl, or R⁷ together with R⁶ may form 3- to 7-membered ring with the bonding nitrogen atom by forming C₂-C₆alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, oxo or thioxo,

R⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, phenyl or phenyl substituted with (Z)_(p1),

R⁹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R²⁴, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,

R¹⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, R¹⁰ together with R⁹ may form 3- to 7-membered ring with the atom bonding them by forming C₂-C₆alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl or C₁-C₆haloalkoxy, formyl, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,

R¹¹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl that may be substituted with (Z)_(p1), R¹¹ together with R⁹ may form 5- to 7-membered ring with the atom bonding them by forming C₂-C₄alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,

R¹² is C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl or phenyl substituted with (Z)_(p1),

R¹³ and R¹⁴ independently of each other are C₁-C₆alkyl or C₁-C₆haloalkyl,

R¹⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxycarbonyl C₁-C₄alkyl, C₁-C₆haloalkoxycarbonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1),

further, in case where Z is present in an adjacent position of R¹⁵, the adjacent R¹⁵ and Z may form 6-membered ring together with the atom bonding them by forming —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C₁-C₄alkyl or C₁-C₄haloalkyl,

R¹⁶ is halogen atom, cyano, nitro, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, hydroxy C₃-C₆cycloalkyl, C₁-C₄alkoxy C₃-C₆cycloalkyl, C₅-C₆cycloalkenyl, —OR²⁵, —N(R²⁶)R²⁵, —SH, —S(O)_(r)R²⁷, —SO₂OH, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸, —C(O)OH, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(O)N(R²⁹)N(R^(28a)) R²⁸, C(S)OR²⁸, —C(S)SR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(O)C(O)OR²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰—C(═NR³¹)N(R²⁹)R³⁰, —C(═NOR³¹)NHR²⁹, —C(═NOR³¹)N(R²⁹)R³⁰, —Si(R¹³)(R¹⁴)R¹², —P(O)(OR²¹)₂, —P(S)(OR²¹)₂, —P(phenyl)₂, —P(O)(phenyl)₂, phenyl, phenyl substituted with (Z)_(p1), naphthyl, D-1 to D-65, E-1 to E-49 or M-1 to M-22,

M-1 to M-22 are partially saturated heterocyclic rings of the following formulae, respectively

R¹⁷ is C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy C₁-C₁₂alkyl, cyano C₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonyl C₁-C₁₂alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₁₂alkenyl, C₃-C₁₂haloalkenyl, C₃-C₁₂alkynyl, C₃-C₁₂haloalkynyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, —C(O)ON═C(CH₃)SCH₃, —C(O)ON═C(SCH₃)C(O)N(CH₃)₂, phenyl or phenyl substituted with (Z)_(p1),

R¹⁸ is C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy C₁-C₁₂alkyl, cyano C₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonyl C₁-C₁₂alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₁₂alkenyl, C₃-C₁₂haloalkenyl, C₃-C₁₂alkynyl, C₃-C₁₂haloalkynyl, phenyl or phenyl substituted with (Z)_(p1), or R¹⁸ together with R¹⁷ may form 5- to 8-membered ring with the nitrogen atom bonding them by forming C₄-C₇alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with C₁-C₄alkyl or C₁-C₄alkoxy,

R¹⁹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NHR²⁹—C(O)N(R²⁹)R²⁸, C(S)OR²⁸, C(S)SR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —S(O)₂R²⁸, —S(O)₂NHR²⁹, —S(O)₂N(R²⁹) R²⁸, —P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30 or E-31,

R^(19a) is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, phenyl C₂-C₄alkenyl, di(C₁-C₆alkyl)amino, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,

R^(19b) is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio or di(C₁-C₆alkyl)amino, or R^(19a) together with R^(19b) may form 4- to 6-membered ring with the carbon atom bonding them by forming C₃-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, formyl, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,

R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, cyano C₁-C₆alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl, or R²⁰ together with R¹⁹ may form 5- to 6-membered ring with the nitrogen atom bonding them by forming C₄-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,

R²¹ is C₁-C₆alkyl or C₁-C₆haloalkyl,

R²² is halogen atom, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxy C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylamino, di(C₁-C₄alkyl)amino, C₁-C₆alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1), when q1, q2, q3 or q4 is an integer of 2 or more,

each R²² may be identical with or different from each other, further in case where two R²²s are present on the same carbon atom, the two R²²s together may form oxo, thioxo, imino, C₁-C₆alkylimino, C₁-C₆alkoxyimino or C₁-C₆alkylidene,

R²³ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl substituted with R³², C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —OH, benzyloxy, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1) or D-5,

R²⁴ is halogen atom, cyano, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,

R²⁵ is hydrogen atom, C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R³², C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R³², C₃-C₈alkenyl, C₃-C₈alkenyl arbitrarily substituted with R³², C₃-C₈alkynyl, C₃-C₈alkynyl arbitrarily substituted with R³², —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(O)C(O)R³³, —C(O)C(O)OR³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³, —Si(R¹³) (R¹⁴)R¹², —P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, D-62, D-63, D-65, E-3 to E-9, E-23 to E-31, E-34 or E-45,

R²⁶ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy, phenyl or phenyl substituted with (Z)_(p1), or R²⁶ together with R²⁵ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, phenyl, phenyl substituted with (Z)_(p1), oxo or thioxo,

R²⁷ is C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R³², C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R³², C₃-C₈alkenyl, C₃-C₈alkenyl arbitrarily substituted with R³², C₃-C₈alkynyl, C₃-C₈alkynyl arbitrarily substituted with R³², —SH, C₁-C₆alkylthio, C₁-C₆haloalkylthio, phenylthio, phenylthio substituted with (Z)_(p1), —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴—C(O)N(R³⁴)R³³, —C(O)C(O)R³³, —C(O)C(O)OR³³, —C(S)R³³, —C(S)OR³³—C(S)SR³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³,

—P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1), D-18, D-21, D-25, D-30 to D-35, D-47, D-50, D-51, E-3 to E-9, E-23 to E-31, E-34 or E-45,

R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R³², C₂-C₆alkenyl C₃-C₈cycloalkyl, C₂-C₆haloalkenyl C₃-C₈cycloalkyl, C₂-C₈alkenyl, C₂-C₈alkenyl arbitrarily substituted with

R³², C₂-C₈alkynyl, C₂-C₈alkynyl arbitrarily substituted with R³², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,

R^(28a) is hydrogen atom or C₁-C₆alkyl,

R²⁹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl substituted with (Z)_(p1), or R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆alkoxy, formyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1),

R³⁰ is C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R³², C₃-C₈cycloalkyl, C₃-C₈alkenyl, C₃-C₈alkenyl arbitrarily substituted with R³², C₃-C₈alkynyl, C₃-C₈alkynyl arbitrarily substituted with R³²,

R³¹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆haloalkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, C₁-C₆haloalkylthio C₁-C₄alkyl, C₁-C₆alkylsulfonyl C₁-C₄alkyl, C₁-C₆haloalkylsulfonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, phenyl or phenyl substituted with (Z)_(p1), or R³¹ together with R³⁰ may form 5- to 7-membered ring with the atom bonding them by forming C₂-C₄alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,

R³² is halogen atom, cyano, nitro, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, —OH, —OR³³, —OC(O)R³³, —OC(O)OR³³, —OC(O)NHR³⁴, —OC(O)N(R³⁴)R³³, —OC(S)NHR³⁴, —OC(S)N(R³⁴)R³³, —SH, —S(O)_(r)R³³, —SC(O)R³³, —SC(O)OR³³, —SC(O)NHR³⁴, —SC(O)N(R³⁴)R³³, —SC(S)NHR³⁴, —SC(S)N(R³⁴)R³³, —NHR³⁴, —N(R³⁴)R³³, —N(R³⁴)CHO, —N(R³⁴)C(O)R³³, —N(R³⁴)C(O)OR³³, —N(R³⁴)C(O)NHR³⁴, —N(R³⁴)C(O)N(R³⁴)R³³, —N(R³⁴)C(S)NHR³⁴, —N(R³⁴)C(S)N(R³⁴)R³³, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(O)C(O)OR³³, —Si(R¹³)(R¹⁴)R¹², —P(O)(OR²¹)₂, —P(S)(OR²¹)₂, —P(phenyl)₂, —P(O)(phenyl)₂, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-4 to E-7, E10 to E-14, E-18, E-19, E-23 to E-28, E-32 to E-38, E-43, E-44 or E-45,

R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkyl arbitrarily substituted with R³⁵, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₂-C₆alkenyl C₃-C₈cycloalkyl, C₂-C₆haloalkenyl C₃-C₈cycloalkyl, C₂-C₈alkenyl, C₂-C₈haloalkenyl, C₃-C₈cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65, E-4 to E-7, E-23 to E-27 or E-28,

R³⁴ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with (Z)_(p1), phenylcarbonyl, phenylcarbonyl substituted with (Z)_(p1), C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, D-62, D-63 or D-65, or R³⁴ together with R³³ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆alkoxy, formyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1),

R³⁵ is cyano, C₃-C₆cycloalkyl, C₃-C₆halocylcoalkyl, E-4 to E-7, E-23 to E-28, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, di(C₁-C₆alkyl)aminocarbonyl, tri(C₁-C₆alkyl)silyl, phenyl, phenyl substituted with (Z)_(p1) or D-1 to D-65,

m is an integer of 0 to 5,

n is an integer of 0 to 4,

p1 is an integer of 1 to 5,

p2 is an integer of 0 to 4,

p3 is an integer of 0 to 3,

p4 is an integer of 0 to 2,

p5 is an integer of 0 or 1,

q1 is an integer of 0 to 3,

q2 is an integer of 0 to 5,

q3 is an integer of 0 to 7,

q4 is an integer of 0 to 9,

r is an integer of 0 to 2, and

t is an integer of 0 or 1.

(2) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (1), wherein

G is an aromatic 6-membered ring shown in any one of G-1 to G-10 or an aromatic 5-membered ring shown in any one of G-11 to G-25

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R⁴, C₂-C₆alkenyl, C₂-C₆alkenyl arbitrarily substituted with R⁴, C₂-C₆alkynyl, C₂-C₆alkynyl arbitrarily substituted with R⁴,

—OH, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —C(O)OR⁹, —C(O)SR⁹,

—C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)=NOR¹¹, —S(O)₂NHR¹⁰, —S(O)₂N(R¹⁰)R⁹,

—Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-60 or E-1 to E-49, when m is an integer of 2 or more, each X may be identical with or different from each other,

further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming

—CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S— or —CH═CHCH═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C₁-C₄alkyl or C₁-C₄haloalkyl,

Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵—NHR⁷, —N(R⁷)R⁶, —N═CHOR⁸, —N═C(R⁹)OR⁸, —C(O)NHR¹⁰,

—C(O)N(R¹⁰)R⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-24, D-30 to D-38, D-43 to D-52 or D-53, when n is an integer of 2 or more, each Y may be identical with or different from each other,

further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-membered ring together with carbon atoms to which the two Ys are bonded by forming

—CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH═N— or —SCH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C₁-C₄alkyl or C₁-C₄haloalkyl,

R¹ is C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R¹⁶, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈alkenyl, C₃-C₈haloalkenyl, phenyl C₃-C₆alkenyl, phenyl C₃-C₆alkenyl substituted with (Z)_(p1), C₃-C₈alkynyl, C₃-C₈haloalkynyl, phenyl C₃-C₆alkynyl, phenyl C₃-C₆alkynyl substituted with (Z)_(p1), C₁-C₆alkoxy, —N(R²⁰)R¹⁹, —N═CHR^(19b),

—N═C(R^(19b))R^(19a), —C(O)N(R¹⁰)R⁹, —C(S)N(R¹⁰)R⁹, —C(═NR¹¹)OR⁹, —C(═NR¹¹)SR⁹, —C(═NR¹¹)N(R¹⁰)R⁹, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-6 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4 to E-9, E-23 to E-28, E-30, E-31, E-34 or E-45,

R² is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, benzyloxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, phenylthio C₁-C₄alkyl, phenylthio C₁-C₄alkyl substituted with (Z)_(p1), cyano C₁-C₆alkyl, nitro C₁-C₆alkyl, C₁-C₄alkylcarbonyl C₁-C₄alkyl, C₁-C₄alkoxycarbony C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —SR⁹, —S(O)₂R⁹, —SN(R¹⁸)R¹⁷, —OH, —OR¹⁹, —NHR²⁰,

N(R²⁰)R¹⁹, —N═CHR^(19b), —N═C(R^(19b))R^(19a), —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹,

or R¹ and R² together form ═C(R^(2a))R^(1a), and further R¹ and R² together may form 3- to 7-membered ring together with the nitrogen atom bonding them by forming C₂ to C₆ alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C₁-C₆alkyl, formyl, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,

R^(1a) and R^(2a) together may form 5- or 6-membered ring together with the carbon atom bonding them by forming C₄ or C₅ alkylene chain or C₄ or C₅ alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms, sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with halogen atom or C₁-C₆alkyl,

R³ is cyano, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —OR⁵, —S(O)_(r)R⁵—N(R¹⁰)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(O)NHR¹⁰,

—C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)═NOR¹¹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D8- to

D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60 or E-4 to E-7, E-23 to E27 or E-28,

R⁴ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OH, —OR⁵, —S(O)_(r)R⁵,

—N(R¹⁰)R⁹, —N(R¹⁰)C(O)R⁹, —N(R¹⁰)C(O)OR⁹, —N(R¹⁰)C(O)SR⁹,

—N(R¹⁰)C(S)OR⁹, —N(R¹⁰)C(S)SR⁹, —N(R¹⁰)S(O)₂R⁹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-5, D-8 to D-38, D-41, D-43, D-44, D-47 to D-52 or D-53,

R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-7, D-9, D-15 to D-23, D-30 to D-35, D-47 to

D-53, E-3 to E-9, E-23 to E-27 or E-28,

R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, —S(O)₂R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or

—C(S)SR⁹,

R⁷ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R⁸ is C₁-C₆alkyl,

R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-6 to D-35, D-38, D-47 to D-54 or D-55,

R¹⁰ is hydrogen atom or C₁-C₆alkyl, or R¹⁰ together with R⁹ may form 5- to 7-membered ring with the nitrogen atom bonding them by forming C₄-C₆alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R¹¹ is C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), phenyl or phenyl substituted with (Z)_(p1), or R¹¹ together with R⁹ may form 5- or 6-membered ring with the atom bonding them by forming C₂-C₃alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl,

R¹² is C₁-C₆alkyl, phenyl or phenyl substituted with (Z)_(p1),

R¹³ and R¹⁴ independently of each other are C₁-C₆alkyl,

R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), phenyl or phenyl substituted with (Z)_(p1),

R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OR²⁵, —N(R²⁶)R²⁵, —SH, —S(O)_(r)R²⁷, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹,

—C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)=NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, —C(═NR³¹)N(R²⁹)R³⁰, —C(═NOR³¹)NHR²⁹, —C(═NOR³¹)N(R²⁹)R³⁰, —Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-60, E-1 to E-49 or M-1 to M-22,

R¹⁷ is C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₆alkoxycarbonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1) or C₁-C₆alkoxycarbonyl,

R¹⁸ is C₁-C₆alkyl, phenyl C₁-C₄alkyl or phenyl C₁-C₄alkylsubstituted with (Z)_(p1), or R¹⁸ together with R¹⁷ may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C₄-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with methyl or methoxy,

R¹⁹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —S(O)₂R²⁸, —S(O)₂NHR²⁹, —S(O)₂N(R²⁹)R²⁸, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30 or E-31,

R^(19a) is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-10, D-15 to D-23, D-47 to D-55, E-4 to E-7, E-23 to E-27 or E-28,

R^(19b) is hydrogen atom or C₁-C₆alkyl, or R^(19a) together with R^(19b) may form 5- or 6-membered ring with the carbon atom bonding them by forming C₄-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ or C₁-C₆alkylsulfonyl,

R²² is halogen atom, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆alkoxycarbonyl,

—C(O)NH₂ or —C(S)NH₂, when q1, q2, q3 or q4 is an integer of 2 or more, each R²² may be identical with or different from each other, further in case where two R²²s are present on the same carbon atom, the two R²²s together may form oxo, thioxo, imino, C₁-C₆alkylimino, C₁-C₆alkoxyimino or C₁-C₆alkylidene,

R²³ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —OH, benzyloxy, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —S(O)₂R³³, phenyl, phenyl substituted with (Z)_(p1) or D-5,

R²⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³, di(C₁-C₆alkyl)phosphoryl, di(C₁-C₆alkyl)thiophosphoryl, tri(C₁-C₄alkyl)silyl, phenyl or phenyl substituted with (Z)_(p1),

R²⁶ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl or C₁-C₆alkoxy, or R²⁶ together with R²⁵ may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C₃-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may substituted with C₁-C₆alkyl, oxo or thioxo,

R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxy C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylcarbonyl C₁-C₄alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl, di(C₁-C₄alkyl)aminocarbonyl C₁-C₄alkyl, tri(C₁-C₄alkyl)silyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkylcarbonyl, C₁-C₆alkylthio, phenylthio, phenylthio substituted with (Z)_(p1),

—C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, phenyl, phenyl substituted with (Z)_(p1), D-21, D-35, D-47 or D-50,

R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-60 or E-1 to E-49,

R²⁹ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, or R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R³⁰ is C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, tri(C₁-C₆alkyl)silyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₈alkenyl, C₃-C₈haloalkenyl, C₃-C₈alkynyl or C₃-C₈haloalkynyl,

R³¹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl or C₃-C₆cycloalkyl, or R³¹ together with R³⁰ may form 5- or 6-membered ring with the atom bonding them by forming C₂-C₃alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl,

R³² is halogen atom, cyano, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, —OR³³, —OC(O)R³³,

—OC(O)NHR³³, —OC(O)N(R³⁴)R³³, —S(O)_(r)R³³, —SC(O)R³³, —SC(O)NHR³³, —SC(O)N(R³⁴)R³³, —N(R³⁴)CHO, —N(R³⁴)C(O)R³³, —N(R³⁴)C(O)OR³³, —C(O)OR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-60 or E-1 to E-49,

R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-13, D-15 to D-18, D-21, D-29 to D-37, D-47 to D-55, E-5, E-7, E-9, E-24, E-25,

E-27, E-28, E-30, E-31 or E-34,

R³⁴ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, or

R³⁴ together with R³³ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom.

(3) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (2), wherein

G is G-1, G-3, G-4, G-13, G-14, G-17, G-18, G-20, G-21 or G-22,

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)═NOR¹¹, —Si(R¹³)(R¹⁴)R¹², E-10, E-12, E-18, E-32, E-35 or E-43, when m is 2 or 3, each X may be identical with or different from each other,

further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CF₂OCF₂—, —OCF₂O—, —CF₂OCF₂O— or —OCF₂CF₂O—,

Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —NHR⁷, —N(R⁷)R⁶, —N═C(R⁹)OR⁸, —C(O)NH₂ or —C(S)NH₂, when n is 2 or 3, each Y may be identical with or different from each other,

R¹ is C₁-C₈alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈alkenyl, C₃-C₈haloalkenyl, C₃-C₈alkynyl, C₃-C₈haloalkynyl,

—N(R²⁰)R¹⁹, —C(O)N(R¹⁰)R⁹, —C(S)N(R¹⁰)R⁹, phenyl substituted with (Z)_(p1), D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4, E-5, E-7, E-8, E-9, E-23 to E-25, E-27, E-28, E-30, E-31 or E-34,

R² is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —OH, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxycarbonyloxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylthio, phenylthio, phenylthio substituted with (Z)_(p1), C₁-C₆alkylsulfonyl, —SN(R¹⁸)R¹⁷, —NHR²⁰, —N═CHR^(19b), —N═C(R^(19b))R^(19a), —C(O)R⁹,

—C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹, or R² together with R¹ may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C₂-C₆alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆halocycloalkyl C₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄haloalkylsulfinyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, cyano C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxy C₁-C₄haloalkyl, C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄alkylsulfinyl C₁-C₄haloalkyl, C₁-C₄alkylsulfonyl C₁-C₄haloalkyl, C₁-C₄haloalkylthio C₁-C₄haloalkyl, C₁-C₄haloalkylsulfinyl C₁-C₄haloalkyl, C₁-C₄haloalkylsulfonyl C₁-C₄haloalkyl, cyano C₁-C₆haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28,

R⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl or tri(C₁-C₆alkyl)silyl,

R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28,

R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, —S(O)₂R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹,

R⁷ is hydrogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,

R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R¹⁰ is hydrogen atom or C₁-C₆alkyl, or R¹⁰ together with R⁹ may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C₄ or C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R¹¹ is C₁-C₆alkyl or C₁-C₆haloalkyl, or R¹¹ together with R⁹ may form 5- or 6-membered ring with the atom bonding them by forming C₂ or C₃alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl,

R¹⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl,

R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OR²⁵, —N(R²⁶)R²⁵, —S(O)_(r)R²⁷, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, —C(═NR³¹)N(R²⁹)R³⁰, —C(═NOR³¹)NHR²⁹, —C(═NOR³¹)N(R²⁹)R³⁰, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16,

R¹⁷ is C₁-C₆alkyl, C₁-C₆alkoxycarbonyl C₁-C₄alkyl or C₁-C₆alkoxycarbonyl,

R¹⁸ is C₁-C₆alkyl or benzyl,

R¹⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₆alkyl, phenyl C₁-C₆alkyl, phenyl C₁-C₆alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NH R²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, C₂-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)_(p1), phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56,

R^(19a) is C₁-C₆alkyl,

R^(19b) is hydrogen atom or C₁-C₆alkyl,

R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl or C₁-C₆alkylsulfonyl,

R²² is C₁-C₄alkyl or C₁-C₄haloalkyl, or two R²²s present on the same carbon atom may together form oxo, or thioxo,

R²³ is hydrogen atom, C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R²⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³, di(C₁-C₆alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)_(p1),

R²⁶ is hydrogen atom or C₁-C₆alkyl, or R²⁶ together with R²⁵ may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C₃-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with C₁-C₆alkyl, oxo or thioxo,

R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl, tri(C₁-C₄alkyl)silyl C₁-C₄alkyl, C₁-C₆alkylthio, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, phenyl, phenyl substituted with (Z)_(p1), D-47 or D-50,

R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl substituted with (Z)_(p1),

R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, or R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,

R³⁰ is C₁-C₆alkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₈alkenyl or C₃-C₈alkynyl,

R³¹ is hydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may form 5- or 6-membered ring with the atom bonding them by forming C₂ or C₃alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl,

R³² is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkoxycarbonyl, —C(O)NH₂, C₁-C₄alkylaminocarbonyl, di(C₁-C₄alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)_(p1),

R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1),

R³⁴ is hydrogen atom or C₁-C₆alkyl,

m is an integer of 1 to 3,

n is an integer of 0 to 2,

q1 is 0,

q2 is an integer of 0 to 3,

q3 is an integer of 0 to 2, and

q4 is an integer of 0 to 2.

(4) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (3), wherein

A¹ is carbon atom or nitrogen atom,

A² and A³ are carbon atom,

G is G-1,

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵ or tri(C₁-C₆alkyl)silyl, when m is 2 or 3, each X may be identical with or different from each other, further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming

—CF₂OCF₂—, —OCF₂O—, —CF₂OCF₂O— or —OCF₂CF₂O—,

Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —NHR⁷, —N(R⁷)R⁶, —C(O)NH₂ or —C(S)NH₂, when n is 2 or 3, each Y may be identical with or different from each other,

R¹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —N(R²⁰)R¹⁹, —C(O)N(R¹⁰)R⁹, —C(S)N(R¹⁰)R⁹, phenyl substituted with (Z)_(p1), D-8, D-10, D-11, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, D-47 to D-54, D-56, D-58, E-4, E-5, E-7 or E-9,

R² is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —OH, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylsulfonyloxy, —NH₂, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹,

R³ is C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxy C₁-C₄haloalkyl, C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄haloalkylthio C₁-C₄haloalkyl, cyano C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,

R⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl or tri(C₁-C₆alkyl)silyl,

R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkynyl or C₃-C₆haloalkynyl,

R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, C₃-C₆halocycloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R⁷ is hydrogen atom or C₁-C₆alkyl,

R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OR²⁵, —N(R²⁶)R²⁵, —S(O)_(r)R²⁷—SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3,

M-5, M-8, M-9 or M-10,

R¹⁹ is C₁-C₆haloalkyl, C₃-C₆cycloalkyl, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3,

D-4, D-21, D-47, D-50, D-51, D-53 or D-54,

R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or C₁-C₆alkylsulfonyl,

R²⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl or C₁-C₆alkylsulfonyl,

R²⁶ is hydrogen atom or C₁-C₆alkyl,

R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl or tri(C₁-C₄alkyl)silyl C₁-C₄alkyl,

R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1),

R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R³⁰ is C₁-C₆alkyl or C₃-C₆cycloalkyl C₁-C₄alkyl,

R³¹ is hydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may form 5- or 6-membered ring with the atom bonding them by forming C₂ or C₃alkylene chain.

(5) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (4), wherein

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxy C₁-C₆haloalkyl, C₁-C₆alkoxy C₁-C₆haloalkyl, C₁-C₆haloalkoxy C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, —OR⁵, —OSO₂R⁵ or —S(O)_(r)R⁵, when m is 2 or 3, each X may be identical with or different from each other,

Y is halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —NHR⁷ or —N(R⁷)R⁶,

R¹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —N(R²⁰)R¹⁹, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 or D-54,

R² is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkynyl, —C(O)R⁹ or —C(O)OR⁹,

R³ is C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,

R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₃haloalkoxy C₁-C₃haloalkyl,

R⁶ is C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R⁹ is C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl,

—C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32,

R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,

R²⁰ is hydrogen atom or C₁-C₆alkyl,

R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R²⁹ is hydrogen atom or C₁-C₆alkyl,

R³⁰ is C₁-C₆alkyl,

R³¹ is hydrogen atom or C₁-C₆alkyl, and

n is an integer of 0 or 1.

(6) 3,5-Bis (substituted aryl) substituted isoxazoline compound of formula (2) or a salt thereof:

wherein

A¹ is carbon atom or nitrogen atom,

X¹ is halogen atom, —SF₅, C₁-C₆haloalkyl, hydroxy C₁-C₆haloalkyl, C₁-C₆alkoxy C₁-C₆haloalkyl, C₁-C₆haloalkoxy C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₁-C₆haloalkoxy, C₁-C₃haloalkoxy C₁-C₃haloalkoxy, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl or C₁-C₆haloalkylsulfonyl,

X² is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, —OR⁵, —OSO₂R⁵ or —S(O)_(r)R⁵, when m1 is 2, each X² may be identical with or different from each other,

Y is halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —NHR⁷ or —N(R⁷)R⁶,

R³ is C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,

R⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl,

R⁶ is C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R⁷ is hydrogen atom or C₁-C₆alkyl,

R is halogen atom, cyano, nitro, —NH₂, halosulfonyloxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy substituted with (Z)_(p1) or —C(O)R^(a),

R^(a) is halogen atom, —OH, C₁-C₆alkoxy, 1-pyrazolyl, 1-imidazolyl or 1-triazolyl,

Z is halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl, when p1 is an integer of 2 or more,

each Z may be identical with or different from each other,

m1 is an integer of 0 to 2,

n is an integer of 0 or 1,

p1 is an integer of 1 or 5, and

r is an integer of 0 to 2.

(7) 3,5-Bis (substituted aryl) substituted isoxazoline compound or the salt thereof as set forth in (6), wherein

(a) in case where R is halosulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenylsulfonyloxy or phenylsulfonyloxy substituted with (Z)_(p1), Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

(b) in case where R is —C(O)R^(a), Y is cyano, nitro, C₁-C₆alkyl, C₁-C₄haloalkyl, C₁-C₆haloalkylthio or C₁-C₆haloalkylsulfonyl,

(c) in case where, R is halogen atom, cyano, nitro or —NH₂, Y is cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆haloalkylthio or C₁-C₆haloalkylsulfonyl.

(8) 4-Hydroxyiminomethyl substituted benzamide compound of formula (3) or a salt thereof:

wherein

A¹ is carbon atom or nitrogen atom,

J is hydrogen atom or halogen atom,

W is oxygen atom or sulfur atom,

Y is halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl or —N(R⁷)R⁶,

R¹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —N(R²⁰)R¹⁹, phenyl substituted with (Z)_(p1), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 or D-54,

R² is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkynyl, —C(O)R⁹ or —C(O)OR⁹,

R⁶ is —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R⁷ is hydrogen atom or C₁-C₆alkyl,

R⁹ is C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32,

D-1 to D-4, D-8 to D-38, D-47 to D-54 and D-55 are aromatic heterocyclic rings of the following formulae, respectively,

Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, —C(O)NH₂, C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl, —C(S)NH₂, —S(O)₂NH₂, C₁-C₆alkylaminosulfonyl or di(C₁-C₆alkyl)aminosulfonyl, when p1, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other,

R¹⁵ is C₁-C₆alkyl, phenyl or phenyl substituted with (Z)_(p1),

E-4, E-5, E-10, E-11 or E-32 is a saturated heterocyclic ring of the following formulae, respectively

R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,

R²⁰ is hydrogen atom or C₁-C₆alkyl,

R²² is C₁-C₄alkyl,

R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R²⁹ is hydrogen atom or C₁-C₆alkyl,

R³⁰ is C₁-C₆alkyl,

R³¹ is C₁-C₆alkyl,

n is an integer of 0 or 1, with a proviso that n is 1 when R¹ and R² are methyl at the same time,

p1 is an integer of 1 to 5,

p2 is an integer of 0 to 4,

p3 is an integer of 0 to 3,

p4 is an integer of 0 to 2,

p5 is an integer of 0 or 1,

q2 is an integer of 0 to 3, and

q3 is an integer of 0 to 2

(9) 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof as set forth in (8), wherein

A¹ is carbon atom,

W is oxygen atom,

Y is halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,

R¹ is C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, D-13 to D-15, D-21, D-47, D-48, D-50 to D-53 or D-54,

R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, E-4, E-5, E-10, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —C(O)N(R²⁹)R²⁸, D-1, D-8, D-15 to D-17, D-21, D-22, D-28, D-29, D-34, D-35, D-38, D-47, D-50, D-51 or D-53.

(10) Substituted alkenylbenzene compound of formula (4):

wherein

X¹ is halogen atom, —SF₅, C₁-C₆haloalkyl, hydroxy C₁-C₆haloalkyl, C₁-C₆alkoxy C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₁-C₆haloalkoxy, C₁-C₃haloalkoxy C₁-C₃haloalkoxy, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl or C₁-C₆haloalkylsulfonyl,

X³ is hydrogen atom, halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy or C₁-C₆alkylthio,

X⁴ is hydrogen atom, halogen atom, cyano, C₁-C₄alkyl, C₁-C₄alkoxy or C₁-C₄haloalkoxy,

R³ is —C(R^(3a))(R^(3b))R^(3c),

R^(3a) and R^(3b) independently of each other are halogen atom, or R^(3a) and R^(3b) together may form 3- to 6-membered ring together with the carbon atom bonding them by forming C₂-C₅haloalkylene chain,

R^(3c) is hydrogen atom, halogen atom, C₁-C₅alkyl, C₁-C₅haloalkyl, C₁-C₄haloalkoxy or C₁-C₄haloalkylthio, with a proviso that in case where X¹ is fluorine atom, chlorine atom or trifluoromethyl and both X² and X³ are hydrogen atom, in case where both X¹ and X² are fluorine atom and X³ is hydrogen atom, and in case where both X¹ and X² are trifluoromethyl and X³ is hydrogen atom, R^(3c) is hydrogen atom, chlorine atom, bromine atom, iodine atom, C₁-C₅alkyl, C₁-C₅haloalkyl, C₁-C₄haloalkoxy or C₁-C₄haloalkylthio.

(11) The substituted alkenylbenzene compound as set forth in (10), wherein

X¹ is halogen atom, —SF₅, C₁-C₆haloalkyl, C₁-C₆haloalkoxy or C₁-C₆haloalkylthio,

X³ is hydrogen atom, halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₆alkoxy,

X⁴ is hydrogen atom or halogen atom,

R^(3a) and R^(3b) are flurine atom,

R^(3c) is hydrogen atom, fluorine atom, chlorine atom, bromine atom or trifluoromethyl, with a proviso that in case where X¹ is fluorine atom, chlorine atom or trifluoromethyl and both X³ and X⁴ are hydrogen atom, in case where both X¹ and X³ are fluorine atom and X⁴ is hydrogen atom, and in case where both X¹ and X³ are trifluoromethyl and X⁴ is hydrogen atom, R^(3c) is hydrogen atom, chlorine atom, bromine atom or trifluoromethyl.

(12) A pesticide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).

(13) An agrochemical containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).

(14) An endo- or ecto-parasiticide for mammals or birds containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).

(15) An insecticide or acaricide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).

EFFECT OF THE INVENTION

The compound according to the present invention has an excellent insecticidal and acaricidal activity for many agricultural insect pests, spider mites, endo- or ecto-parasiticide for mammals or birds, and exerts a control effect sufficient for pest insects that acquire resistance against exiting insecticides. Further, the compound has little adverse affect on mammals, fishes and beneficial insects, and has a low persistency and a low impact on the environment. Therefore, the present invention can provide a useful and novel pesticide.

BEST MODE FOR CARRYING OUT THE INVENTION

Active compounds used as the pesticide in the present invention are generally the compounds of formulae (1) to (5) mentioned above, and the compounds of formulae (6) to (11) mentioned above are novel production intermediates used for the production of these active compounds. These intermediates contain specific compounds themselves having control activity against specific pests that can be used as a control agent for the pest.

In the compounds included in the present invention, some compounds have geometrical isomers of E-form and Z-form depending on the kind of substituents. The present invention includes these E-forms, Z-forms and mixtures containing E-form and Z-form in an arbitrary proportion. In addition, the compounds included in the present invention have optically active forms resulting from the presence of 1 or more asymmetric carbon atoms, and the present invention includes all optically active forms or racemates. Further, in the compounds of formula (1) according to the present invention, some compounds wherein R² is hydrogen atom are present in tautomer, and the present invention includes these structures,

The compounds included in the present invention can be converted to acid addition salts for example salts of hydrohalide acid such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydriodic acid or the like, salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid or the like, salts of sulfonic acid such as methansulfonic acid, ethanesulfonic acid, trufluoromethansulfonic acid, benzene sulfonic acid, p-toluene sulfonic acid or the like, salts of carboxylic acid such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or the like, or salts of amino acid such as glutamic acid, aspartic acid or the like, according to a conventional method.

The compounds included in the present invention can be converted to metal salts for example salts of alkali metal such as lithium, sodium, potassium, salts of alkaline earth metal such as calcium, barium, magnesium, or salts of aluminum, according to a conventional method.

Hereinafter, concrete examples of each substituent shown in the specification are described. In the specification, “n-” means normal, “i-” means iso, “s-” means secondary, and “t-” means tertiary, and “Ph” means phenyl.

Halogen atom in the compounds of the present invention includes fluororine atom, chlorine atom, bromine atom and iodine atom. In the interim, the indication of “halo” in the specification also means these halogen atoms.

In the specification, the indication of “C_(a)-C_(b)alkyl” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of a to b, and includes for example methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, 5-methylhexyl, 2-ethylpentyl, octyl, 2-ethylhexyl, nonyl, 2-methyloctyl, decyl, 2-methylnonyl, undecyl, 2-methyldecyl, dodecyl and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkyl” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2-dichloroethyl, 2-bromo-2-fluoroethyl, 2-bromo-2-chloroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 2-bromo-2-chloro-2-fluoroethyl, 2-bromo-2,2-dichloroethyl, pentafluoroethyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2-chloro-3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl, 2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 5-chloro-2,2,3,4,4,5,5-heptafluoropentyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “cyano C_(a)-C_(b)alkyl” means straight-chain or branched-chain alkyl groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a cyano group (cyano groups). Concrete examples thereof are for example cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 2-cyanobutyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkyl” means cyclic hydrocarbon groups having carbon atom number of a to b, and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number. Concrete examples thereof are for example cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, bicyclo[2.2.1]heptan-2-yl and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)halocycloalkyl” means cyclic hydrocarbon groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms), and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number. The substitution for halogen atom may be in the ring structure moiety, the side chain moiety or both of them. Further, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, 2,2-dichloro-3,3-dimethylcyclopropyl, 2,2,3,3-tetrafluorocyclobutyl, 2-trifluoromethylcyclohexyl, 3-trifluoromethylcyclohexyl, 4-trifluoromethylcyclohexyl and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkenyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds. Concrete examples thereof are for example vinyl, 1-propenyl, 1-methylethenyl, 2-propenyl, 2-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-hexenyl, 2-methyl-2-pentenyl, 2,4-dimethyl-2,6-heptadienyl, 3,7-dimethyl-2,6-octadienyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)halolkenyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2,3,3-trifluoro-2-propenyl, 1-trifluoromethylvinyl, 2,3,3-trichloro-2-propenyl, 2-bromo-2-butenyl, 3-bromo-2-methyl-2-propenyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkenyl” means cyclic unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number, and further the double bond may be either endo- or exo-form. Concrete examples thereof are for example 2-cyclopenten-1-yl, 3-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, bicyclo[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloycloalkenyl” means cyclic unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms), and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number, and further the double bond may be either endo- or exo-form. The substitution for halogen atom may be in the ring structure moiety, the side chain moiety or both of them. Further, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2-chlorobicyclo[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkynyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more triple bonds. Concrete examples thereof are for example ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 2-pentynyl, 1-methyl-2-butynyl, 2-hexynyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)halolkynyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more triple bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkoxy” means alkyl-O-groups wherein the alkyl has carbon atom number of a to b, and includes for example methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, s-butyloxy, i-butyloxy, t-butyloxy, n-pentyloxy, n-hexyloxy and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkoxy” means haloalkyl-O-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2-dichloro-1,1,2-trifluoroethoxy, pentafluoroethoxy, 2,2,2-trichloro-1,1-difluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 2,2,3,3-tetrafluoropropyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, 2,2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropyloxy, 2-bromo-1,1,2,3,3,3-hexafluoropropyloxy, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylthio” means alkyl-S— groups wherein the alkyl has carbon atom number of a to b, and includes for example methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, i-butylthio, t-butylthio, n-pentylthio, n-hexylthio and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylthio” means haloalkyl-S-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethylthio, trifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 1,1,2-trifluoro-2-chloroethylthio, pentafluoroethylthio, 2-bromo-1,1,2,2-tetrafluoroethylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-trifluoromethylthio, 1,2,2,2-tetrafluoro-1-trifluoroethylthio, nonafluorobutylthio, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylsulfinyl” means alkyl-S(O)-groups wherein the alkyl has carbon atom number of a to b, and includes for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, i-butylsulfinyl, t-butylsulfinyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylsulfinyl” means haloalkyl-S(O)-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethylsulfinyl, trifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-bromo-1,1,2,2-tetrafluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethylsulfinyl, nonafluorobutylsulfinyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylsulfonyl” means alkyl-SO₂-groups wherein the alkyl has carbon atom number of a to b, and includes for example methanesulfonyl, ethanesulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, i-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl, n-hexylsulfonyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylsulfonyl” means haloalkyl-SO₂-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethanesulfonyl, trifluoromethanesulfonyl, chlorodifluoromethanesulfonyl, bromodifluoromethanesulfonyl, 2,2,2-trifluoroethanesulfonyl, 1,1,2,2-tetrafluoroethanesulfonyl, 1,1,2-trifluoro-2-chloroethanesulfonyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylamino” means amino groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, t-butylamino, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “di(C_(a)-C_(b)alkyl)amino” means amino groups, which both hydrogen atoms are substituted with the above-mentioned alkyl groups having carbon atom number of a to b that may be identical with or different from each other, and includes for example dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, n-butyl(methyl)amino, i-butyl(methyl)amino, t-butyl(methyl)amino, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylcarbonyl” means alkyl-C(O)-groups wherein the alkyl has carbon atom number of a to b, and includes for example CH₃C(O)—, CH₃CH₂C(O)—, CH₃CH₂CH₂C(O)—, (CH₃)₂CHC(O)—, CH₃(CH₂)₃C(O)—, (CH₃)₂CHCH₂C(O)—, CH₃CH₂CH(CH₃)C(O)—, (CH₃)₃CC(O)—, CH₃(CH₂)₄C(O)—, CH₃(CH₂)₅C(O)—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylcarbonyl” means haloalkyl-C(O)-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example FCH₂C(O)—, ClCH₂C(O)—, F₂CHC(O)—, Cl₂CHC(O)—, CF₃C(O)—, ClCF₂C(O)—, BrCF₂C(O)—, CCl₃C(O)—, CF₃CF₂C(O)—, ClCH₂CH₂CH₂C(O)—, CF₃CF₂CF₂C(O)—, ClCH₂C(CH₃)₂C(O)—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkoxycarbonyl” means alkyl-O—C(O)-groups wherein the alkyl has carbon atom number of a to b, and includes for example CH₃OC(O)—, CH₃CH₂OC(O)—, CH₃CH₂CH₂OC(O)—, (CH₃)₂CHOC(O)—, CH₃(CH₂)₃OC(O)—, (CH₃)₂CHCH₂OC(O)—, (CH₃)₃COC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkoxycarbonyl” means haloalkyl-O—C(O)-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example ClCH₂CH₂OC(O)—, CF₃CH₂OC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylaminocarbonyl” means carbamoyl groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example CH₃NHC(O)—, CH₃CH₂NHC(O)—, CH₃CH₂CH₂NHC(O)—, (CH₃)₂CHNHC(O)—, CH₃(CH₂)₃NHC(O)—, (CH₃)₂CHCH₂NHC(O)—, CH₃CH₂CH(CH₃)NHC(O)—, (CH₃)₃CNHC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylaminocarbonyl” means carbamoyl groups, which either hydrogen atom is substituted with the above-mentioned haloalkyl group having carbon atom number of a to b, and includes for example 2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluorocarbamoyl, 2,2,2-trifluoroethylcarbamoyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “di(C_(a)-C_(b)alkyl)aminocarbonyl” means carbamoyl groups, which both hydrogen atoms are substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example (CH₃)₂NC(O)—, CH₃CH₂N(CH₃)C(O)—, (CH₃CH₂)₂NC(O)—, (CH₃CH₂CH₂)₂NC(O)—, (CH₃CH₂CH₂CH₂)₂NC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylaminosulfonyl” means sulfamoyl groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example CH₃NHSO₂—, CH₃CH₂NHSO₂—, CH₃CH₂CH₂NHSO₂—, (CH₃)₂CHNHSO₂—, CH₃(CH₂)₃NHSO₂—, (CH₃)₂CHCH₂NHSO₂—, CH₃CH₂CH(CH₃)NHSO₂—, (CH₃)₃CNHSO₂, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “di(C_(a)-C_(b)alkyl)aminosulfonyl” means sulfamoyl groups, which both hydrogen atoms are substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example (CH₃)₂NSO₂—, CH₃CH₂N(CH₃)SO₂—, (CH₃CH₂)₂NSO₂—, (CH₃CH₂CH₂)₂NSO₂—, (CH₃CH₂CH₂CH₂)₂NSO₂—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “tri(C_(a)-C_(b)alkyl)silyl” means silyl groups substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, t-butyldimethylsilyl, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylcarbonyloxy” means alkylcarbonyl-O-groups wherein the alkyl has carbon atom number of a to b, and includes for example CH₃C(O)—O—, CH₃CH₂C(O)—O—, CH₃CH₂CH₂C(O)—O—, (CH₃)₂CHC(O)—O—, CH₃(CH₂)₃C(O)—O—, (CH₃)₂CHCH₂C(O)—O—, CH₃CH₂CH(CH₃)C(O)—O—, (CH₃)₃CC(O)—O—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylsulfonyloxy” means alkylsulfonyl-O-groups wherein the alkyl has carbon atom number of a to b, and includes for example CH₃SO₂—O—, CH₃CH₂SO₂—O—, CH₃CH₂CH₂SO₂—O—, (CH₃)₂CHSO₂—O—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylsulfonyloxy” means haloalkylsulfonyl-O-groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethanesulfonyl-O—, trifluoromethanesulfonyl-O—, chlorodifluoromethanesulfonyl-O—, bromodifluoromethanesulfonyl-O—, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkyl C_(d)-C_(e)alkyl”, “C_(a)-C_(b)halocycloalkyl C_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkoxy C_(d)-C_(e)alkyl”, “C_(a)-C_(b)haloalkoxy C_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkylthio C_(d)-C_(e)alkyl”, “C_(a)-C_(b)haloalkylthio C_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkylsulfinyl C_(d)-C_(e)alkyl”, “C_(a)-C_(b)haloalkylsulfinyl C_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkylsulfonyl C_(d)-C_(e)alkyl”, “C_(a)-C_(b)haloalkylsulfonyl C_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkoxycarbonyl C_(d)-C_(e)alkyl”, “phenyl C_(d)-C_(e)alkyl” or “phenyl C_(d)-C_(e)alkyl substituted with (Z)_(p1)” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with the C_(a)-C_(b)cycloalkyl, C_(a)-C_(b)halocycloalkyl, C_(a)-C_(b)alkoxy, C_(a)-C_(b)haloalkoxy, C_(a)-C_(b)alkylthio, C_(a)-C_(b)haloalkylthio, C_(a)-C_(b)alkylsulfinyl, C_(a)-C_(b)haloalkylsulfinyl, C_(a)-C_(b)alkylsulfonyl, C_(a)-C_(b)haloalkylsulfonyl, C_(a)-C_(b)alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1) that has the meaning mentioned above, respectively. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkyl arbitrarily substituted with R⁴”, “C_(a)-C_(b)alkyl arbitrarily substituted with R¹⁶”, “C_(a)-C_(b)alkyl arbitrarily substituted with R²⁴”, “C_(a)-C_(b)alkyl arbitrarily substituted with R³²”, or “C_(a)-C_(b)alkyl arbitrarily substituted with R³⁵” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R⁴, R¹⁶, R²⁴, R³² or R³⁵. It is selected from the scope of the indicated carbon atom number.

In this case, when two or more substituents R⁴, R¹⁶, R²⁴, R³² or R³⁵ are present on the C_(a)-C_(b)alkyl, respective R⁴, R¹⁶, R²⁴, R³² or R³⁵ may be identical with or different from each other.

In the specification, the indication of “hydroxy C_(d)-C_(e)cycloalkyl”, “C_(a)-C_(b)alkoxy C_(d)-C_(e)cycloalkyl”, “C_(a)-C_(b)alkenyl C_(d)-C_(e)cycloalkyl” or “C_(a)-C_(b)haloalkenyl C_(d)-C_(e)cycloalkyl” means the cycloalkyl having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with C_(a)-C_(b)alkoxy, C_(a)-C_(b)alkenyl, C_(a)-C_(b)haloalkenyl or hydroxy. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkyl arbitrarily substituted with R⁴”, “C_(a)-C_(b)cycloalkyl arbitrarily substituted with R¹⁶”, “C_(a)-C_(b)cycloalkyl arbitrarily substituted with R²⁴” or “C_(a)-C_(b)cycloalkyl arbitrarily substituted with R³²” means the cycloalkyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R⁴, R¹⁶, R²⁴ or R³². The substitution for R⁴, R¹⁶, R²⁴ or R³² may be in the ring structure moiety, the side chain moiety or both of them. In this case, when two or more substituents R⁴, R¹⁶, R²⁴ or R³² are present on the C_(a)-C_(b)cycloalkyl, respective R⁴, R¹⁶, R²⁴ or R³² may be identical with or different from each other.

In the specification, the indication of “phenyl C_(a)-C_(b)alkenyl” or “phenyl C_(a)-C_(b)alkenyl substituted with (Z)_(p1)” means the alkenyl having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z)_(p1). It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkenyl arbitrarily substituted with R⁴”, “C_(a)-C_(b)alkenyl arbitrarily substituted with R¹⁶”, “C_(a)-C_(b)alkenyl arbitrarily substituted with R²⁴” or “C_(a)-C_(b)alkenyl arbitrarily substituted with R³²” means the alkenyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R⁴, R¹⁶, R²⁴ or R³². It is selected from the scope of the indicated carbon atom number. In this case, when two or more substituents R⁴, R¹⁶, R²⁴ or R³² are present on the C_(a)-C_(b)alkenyl, respective R⁴, R¹⁶, R²⁴ or R³² may be identical with or different from each other.

In the specification, the indication of “phenyl C_(a)-C_(b)alkynyl” or “phenyl C_(a)-C_(b)alkynyl substituted with (Z)_(p1)” means the alkynyl having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z)_(p1). It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkynyl arbitrarily substituted with R⁴”, “C_(a)-C_(b)alkynyl arbitrarily substituted with R¹⁶”, “C_(a)-C_(b)alkynyl arbitrarily substituted with R²⁴” or “C_(a)-C_(b)alkynyl arbitrarily substituted with R³²” means the alkynyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R⁴, R¹⁶, R²⁴ or R³². It is selected from the scope of the indicated carbon atom number. In this case, when two or more substituents R⁴, R¹⁶, R²⁴ or R³² are present on the C_(a)-C_(b)alkenyl, respective R⁴, R¹⁶, R²⁴ or R³² may be identical with or different from each other.

In the specification, concrete examples of the indication of “R¹ and R² together may form 3- to 8-membered ring together with the nitrogen atom bonding them by forming C₂ to C₇ alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”,

“R¹⁰ together with R⁹ may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C₂-C₆alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”, “R¹⁸ together with R¹⁷ may form 5- to 8-membered ring with the nitrogen atom bonding them by forming C₄-C₇alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom”, “R²⁶ together with R²⁵ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom”, “R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”, “R³⁴ together with R³³ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom”, are for example aziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine, imidazolidine, piperidine, morpholine, thiomorpholine, piperazine, homopiperidine, heptamethyleneimine, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, concrete examples of the indication of “R⁷ together with R⁶ may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C₂-C₆alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom” are for example aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidin-2-one, thiazoridine, thiazoridin-2-one, imidazolidine, imidazolidin-2-one, piperidine, piperidin-2-one, morpholine, tetrahydro-1,3-oxadin-2-one, thiomorpholine, tetrahydro-1,3-thiazin-2-one, piperazine, tetrahydropyrimidin-2-one, homopiperidine, homopiperidin-2-one, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, concrete examples of the indication of “R¹¹ together with R⁹ may form 5- to 7-membered ring with the atom bonding them by forming C₂-C₄alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom” are for example isoxazoline, oxazoline, thiazoline, imidazoline, 1,4,2-dioxazoline, 1,4,2-oxathiazoline, 1,2,4-oxadiazoline, dihydro-1,2-oxadine, dihydro-1,3-oxadine, dihydro-1,3-thiazine, 3,4,5,6-tetrahydropyrimidine, dihydro-1,4,2-dioxadine, dihydro-1,4,2-oxathiazine, dihydro-4H-1,2,4-oxadiazine, tetrahydro-1,2-oxazepine, and the like. It is selected from the scope of the indicated carbon atom number.

In the specification, concrete examples of the indication of “R³¹ together with R³⁰ may form 5- to 7-membered ring with the atom bonding them by forming C₂-C₄alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom” are for example oxazoline, thiazoline, imidazoline, dihydro-1,3-oxazine, dihydro-1,3-thiazine, 3,4,5,6-tetrahydropyrimidine, dihydro-1,4,2-dioxadine, and the like. It is selected from the scope of the indicated carbon atom number.

In the compounds included in the present invention, the combination of the atoms of A¹, A² and A³ includes for example the following groups.

That is, A-I: A¹, A² and A³ are carbon atoms. A-II: A¹ is nitrogen atom, A² and A³ are carbon atoms. A-III: A² is nitrogen atom, A¹ and A³ are carbon atoms. A-IV: A¹ and A³ are nitrogen atom, A² is carbon atom. A-V: A² and A³ are nitrogen atom, A¹ is carbon atom.

In the compounds included in the present invention, the substituent G includes for example aromatic 6-membered rings shown in any one of G-1 to G-10 and aromatic 5-membered rings shown in any one of G-11 to G-25. Among them, aromatic 6-membered rings shown in G-1, G-3 and G-4 and aromatic 5-membered rings shown in any one of G-13, G-14, G-17, G-18, G-20, G-21 and G-22 are preferable, and aromatic 6-membered ring shown in G-1 is particularly preferable.

In the compounds included in the present invention, the substituent W includes for example oxygen atom or sulfur atom.

In the compounds included in the present invention, the substituent X includes for example the following groups. In each case mentioned below, when m is an integer of 2 or more, Xs may be identical with or different from each other.

That is, X-I: halogen atom and C₁-C₆haloalkyl. X-II: halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆alkylsulfonyloxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl and C₁-C₆alkylsulfonyl. X-III: halogen atom, C₁-C₆haloalkyl, C₁-C₆haloalkoxy, C₁-C₃haloalkoxy C₁-C₃haloalkoxy, C₁-C₆haloalkylsulfonyloxy, C₁-C₆haloalklylthio, C₁-C₆haloalkylsulfinyl and C₁-C₆haloalkylsulfonyl. X-IV: halogen atom, C₁-C₆haloalkyl, cyano, nitro, —SF₅ and —Si(R¹³)(R¹⁴)R¹² wherein R¹² is C₁-C₆alkyl, phenyl or phenyl substituted with (Z)_(p1), R¹³ and R¹⁴ independently of each other are C₁-C₆alkyl. X-V: halogen atom and C₁-C₆alkyl arbitrarily substituted with R⁴ wherein R⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl or tri(C₁-C₆alkyl)silyl. X-VI: halogen atom, C₁-C₆haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, E-10, E-12, E-18, E-32, E-35 and E-43. X-VII: halogen atom, C₁-C₆haloalkyl, —OR⁵, —OSO₂R⁵ and —S(O)_(r)R⁵ wherein R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2. X-VIII: halogen atom, C₁-C₆haloalkyl, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹ and —C(R⁹)═NOR¹¹ wherein R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl or C₃-C₈halocycloalkyl, R¹⁰ is hydrogen atom or C₁-C₆alkyl, or R¹⁰ together with R⁹ may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C₄-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R¹¹ is C₁-C₆alkyl or C₁-C₆haloalkyl, or R¹¹ together with R⁹ may form 5- or 6-membered ring with the atom bonding them by forming C₂-C₃alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl. X-IX: m is 2, two adjacent Xs form 5- or 6-membered ring with the carbon atom bonding them by forming —CF₂OCF₂—, —OCF₂O—, —CF₂OCF₂O— or —OCF₂CF₂O—.

In the compounds included in the present invention, m indicating the number of substituent X is an integer of 0 to 5. Among them, m is preferably 1, 2 and 3.

In the compounds included in the present invention, the substituent Y includes for example the following groups. In each case mentioned below, when n is an integer of 2 or more, Ys may be identical with or different from each other.

That is, Y-I: halogen atom, C₁-C₆alkyl and C₁-C₆haloalkyl. Y-II: halogen atom, C₁-C₆alkyl, cyano, nitro, —C(O)NH₂ and —C(S)NH₂. Y-III: halogen atom, C₁-C₆alkyl and C₁-C₆alkyl arbitrarily substituted with C₁-C₆alkyl and R⁴ wherein R⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl or tri(C₁-C₆alkyl)silyl. Y-IV: halogen atom, C₁-C₆alkyl, —OR⁵, —OSO₂R⁵ and —S(O)_(r)R⁵ wherein R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2. Y-V: halogen atom, C₁-C₆alkyl, —NHR⁷, —N(R⁷)R⁶ wherein R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, —S(O)₂R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹, R⁷ is hydrogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl, R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl or C₃-C₈halocycloalkyl and —N═C(R⁹)OR⁸ wherein R⁸ is C₁-C₆alkyl, R⁹ is C₁-C₆alkyl or C₁-C₆haloalkyl. Y-VI: halogen atom, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆alkylamino and di(C₁-C₆alkyl)amino.

In the compounds included in the present invention, n indicating the number of substituent Y is an integer of 0 to 4. Among them, n is preferably 0 and 1.

In the compounds included in the present invention, the substituent R¹ includes for example the following groups.

That is, R¹-I: C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶ (wherein R¹⁶ is halogen atom, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10), C₃-C₈cycloalkyl and C₃-C₈halocycloalkyl. R¹-II: C₁-C₆alkyl arbitrarily substituted with —OR²⁵ wherein R²⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl or C₁-C₆alkylsulfonyl. R¹-III: C₁-C₆alkyl arbitrarily substituted with —N(R²⁶)R²⁵ wherein R²⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl or C₁-C₆alkylsulfonyl, R²⁶ is hydrogen or C₁-C₆alkyl. R¹-IV: C₁-C₆alkyl arbitrarily substituted with —S(O)_(r)R²⁷ wherein R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl or tri(C₁-C₄alkyl)silyl C₁-C₄alkyl, r is an integer of 0 to 2. R¹-V: C₁-C₆alkyl arbitrarily substituted with R¹⁶ wherein R¹⁶ is cyano, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰ or —C(═NR³¹)SR³⁰, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, R³⁰ is C₁-C₆alkyl or C₃-C₆cycloalkyl C₁-C₄alkyl, R³¹ is hydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may for 5- or 6-membered ring with the atom bonding them by forming C₂-C₃alkylene chain. R¹-VI: C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl substituted with (Z)_(p1), D-8, D-10, D-11, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, D-47 to D-54, D-56, D-58, E-4, E-5, E-7 and E-9. R¹-VII: —N(R²⁰)R¹⁹ wherein R¹⁹ is C₁-C₆haloalkyl, C₃-C₆cycloalkyl, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or C₁-C₆alkylsulfonyl, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl. R¹-VIII: C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶ (wherein R¹⁶ is cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, R²⁹ is hydrogen atom or C₁-C₆alkyl, R³⁰ is C₁-C₆alkyl, R³¹ is hydrogen or C₁-C₆alkyl), C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —N(R²⁰)R¹⁹ (wherein R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R²⁰ is hydrogen atom or C₁-C₆alkyl, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl), phenyl substituted with (Z)_(p1), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.

R¹-IX: C₁-C₆haloalkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶ (wherein R¹⁶ is cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, R²⁹ is hydrogen atom or C₁-C₆alkyl, R³⁰ is C₁-C₆alkyl, R³¹ is hydrogen or C₁-C₆alkyl), C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —N(R²⁰)R¹⁹ (wherein R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R²⁰ is hydrogen atom or C₁-C₆alkyl, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl), phenyl substituted with (Z)_(p1), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.

R¹-X: C₁-C₈haloalkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶ (wherein R¹⁶ is C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, —C(O)NH₂, —C(O)NHR²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, D-1 to D-4, D-8 to D-38, D-47 to D-54, E-4 to E-7, E-10, E-11 or E-32, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, R³⁰ is C₁-C₆alkyl, R³¹ is hydrogen or C₁-C₆alkyl), C₃-C₆cycloalkyl, E-4, E-5, C₃-C₈alkenyl, C₃-C₈haloalkenyl, C₃-C₈alkynyl, —N(R²⁰)R¹⁹ (wherein R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R²⁰ is hydrogen atom or C₁-C₆alkyl, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54. R¹-XI: C₁-C₆alkyl and phenyl C₁-C₆alkyl. R¹-XII: C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R¹⁶ (wherein R¹⁶ is halogen atom, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16), C₃-C₈cycloalkyl and C₃-C₈halocycloalkyl. R¹-XIII: C₁-C₈alkyl arbitrarily substituted with —OR²⁵ wherein R²⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, —C(O)R³³, —C(O)OR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³, di(C₁-C₆alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)_(p1), R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1), R³⁴ is hydrogen atom or C₁-C₆alkyl. R¹-XIV: C₁-C₈alkyl arbitrarily substituted with —N(R²⁶)R²⁵ wherein R²⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³ or —S(O)₂N(R³⁴)R³³, R²⁶ is hydrogen atom or C₁-C₆alkyl, or R²⁶ together with R²⁵ may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C₃-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with C₁-C₆alkyl, oxo or thioxo, R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1), R³⁴ is hydrogen atom or C₁-C₆alkyl. R¹-XV: C₁-C₈alkyl arbitrarily substituted with —S(O)_(r)R²⁷ wherein R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl, tri(C₁-C₄alkyl)silyl C₁-C₄alkyl, C₁-C₆alkylthio, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, phenyl, phenyl substituted with (Z)_(p1), D-47 or D-50, R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1), R³⁴ is hydrogen atom or C₁-C₆alkyl, r is an integer of 0 to 2. R¹-XVI: C₁-C₈alkyl arbitrarily substituted with R¹⁶ wherein R¹⁶ is cyano, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, —C(═NR³¹)N(R³⁰)R²⁹, —C(═NOR³¹)NHR²⁹ or —C(═NOR³¹)N(R³⁰)R²⁹, R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkenyl, phenyl or phenyl substituted with (Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, or R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R³⁰ is C₁-C₆alkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₈alkenyl or C₃-C₈alkynyl, R³¹ is hydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may form 5- or 6-membered ring with the atom bonding them by forming C₂-C₃alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl, R³² is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkoxycarbonyl, —C(O)NH₂, C₁-C₄alkylaminocarbonyl, di(C₁-C₄alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)_(p1). R¹-XVII: C₃-C₈alkenyl, C₃-C₈haloalkenyl, C₃-C₈alkynyl, C₃-C₈haloalkynyl, phenyl substituted with (Z)_(p1), D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4, E-5, E-7, E-9, E-23 to E-25, E-27, E-28, E-30, E-31 and E-34. R¹-XVIII: —N(R²⁰)R¹⁹ wherein R¹⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₆alkyl, phenyl C₁-C₆alkyl, phenyl C₁-C₆alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)_(p1), phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56, R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl or C₁-C₆alkylsulfonyl, R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³², C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl substituted with (Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R³² is hydrogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkoxycarbonyl, —C(O)NH₂, C₁-C₄alkylaminocarbonyl, di(C₁-C₄alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)_(p1).

In the compounds included in the present invention, the substituent R² includes for example the following groups.

That is, R²-I: hydrogen atom. R²-II: C₁-C₆alkyl, C₁-C₆haloalkyl and C₃-C₆cycloalkyl. R²-III: C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl and cyano C₁-C₆alkyl. R²-IV: C₃-C₆alkenyl and C₃-C₆alkynyl. R²-V: —OH, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxycarbonyloxy and C₁-C₆alkylsulfonyloxy. R²-VI: C₁-C₆haloalkylthio, phenylthio, phenylthio substituted with (Z)_(p1) and —SN(R¹⁸)R¹⁷ wherein R¹⁷ is C₁-C₆alkyl, C₁-C₆alkoxycarbonyl C₁-C₄alkyl or C₁-C₆alkoxycarbonyl, R¹⁸ is C₁-C₆alkyl or benzyl. R²-VII: —NHR²⁰ (wherein R²⁰ is hydrogen atom, C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or C₁-C₆alkylsulfonyl), —N═CHR^(19b) and —N═C(R^(19b))R^(19a) wherein R^(19a) is C₁-C₆alkyl, R^(19b) is hydrogen atom or C₁-C₆alkyl. R²-VIII: —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ (wherein R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl) and C₁-C₆alkylsulfonyl. R²-IX: 3- to 7-membered ring that R² forms together with R¹ is aziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine, piperidine, morpholine, thiomorpholine and homopiperidine. R²-X: hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —OH, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylsulfonyloxy, —NH₂, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ and —C(S)SR⁹ wherein R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl.

R²-XI: hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkynyl, —C(O)R⁹ and —C(O)OR⁹ wherein R⁹ is C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl.

In the compounds included in the present invention, the substituent R³ includes for example the following groups.

That is, R³-I: C₁-C₆haloalkyl and C₃-C₈halocycloalkyl. R³-II: C₁-C₆alkyl, C₃-C₈cycloalkyl, E-4 to E-7, E-23 to E-27 and E-28. R³-III: C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxy C₁-C₄haloalkyl, C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄alkylsulfinyl C₁-C₄haloalkyl, C₁-C₄alkylsulfonyl C₁-C₄haloalkyl, C₁-C₄haloalkylthio C₁-C₄haloalkyl, C₁-C₄haloalkylsulfinyl C₁-C₄haloalkyl, C₁-C₄haloalkylsulfonyl C₁-C₄haloalkyl and cyano C₁-C₆haloalkyl. R³-IV: C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆halocycloalkyl C₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄haloalkylsulfinyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl and cyano C₁-C₆alkyl. R³-V: C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxy C₁-C₄haloalkyl, C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄haloalkylthio C₁-C₄haloalkyl, cyano C₁-C₆haloalkyl and C₃-C₈halocycloalkyl. R³-VI: C₁-C₆haloalkyl. R³-VII: C₁-C₆alkyl arbitrarily substituted with two or more arbitrary halogen atoms.

Each group showing the scope of each substituent in the compounds included in the present invention can be arbitrarily combined one another, and all combination thereof falls within the scope of the present invention. Examples of the combination of the scope of X, Y and R¹ include for example the combination shown in Table 1. In the meantime, the combination of Table 1 is for illustrative purposes, and the present invention is not limited thereto.

TABLE 1 X Y R¹ X-I Y-I R¹-I X-I Y-I R¹-II X-I Y-I R¹-III X-I Y-I R¹-IV X-I Y-I R¹-V X-I Y-I R¹-VI X-I Y-I R¹-VII X-I Y-I R¹-VIII X-I Y-I R¹-IX X-I Y-I R¹-X X-I Y-I R¹-XI X-I Y-II R¹-I X-I Y-II R¹-II X-I Y-II R¹-III X-I Y-II R¹-IV X-I Y-II R¹-V X-I Y-II R¹-VI X-I Y-II R¹-VII X-I Y-II R¹-VIII X-I Y-II R¹-IX X-I Y-II R¹-X X-I Y-II R¹-XI X-I Y-III R¹-I X-I Y-III R¹-VII X-I Y-III R¹-VIII X-I Y-III R¹-IX X-I Y-III R¹-X X-I Y-IV R¹-I X-I Y-IV R¹-II X-I Y-IV R¹-III X-I Y-IV R¹-IV X-I Y-IV R¹-V X-I Y-IV R¹-VI X-I Y-IV R¹-VII X-I Y-IV R¹-VIII X-I Y-IV R¹-IX X-I Y-IV R¹-X X-I Y-IV R¹-XI X-I Y-V R¹-I X-I Y-V R¹-II X-I Y-V R¹-III X-I Y-V R¹-IV X-I Y-V R¹-V X-I Y-V R¹-VI X-I Y-V R¹-VII X-I Y-V R¹-VIII X-I Y-V R¹-IX X-I Y-V R¹-X X-I Y-V R¹-XI X-I Y-VI R¹-I X-I Y-VI R¹-II X-I Y-VI R¹-III X-I Y-VI R¹-IV X-I Y-VI R¹-V X-I Y-VI R¹-VI X-I Y-VI R¹-VII X-I Y-VI R¹-VIII X-I Y-VI R¹-IX X-I Y-VI R¹-X X-I Y-VI R¹-XI X-II Y-I R¹-I X-II Y-I R¹-II X-II Y-I R¹-III X-II Y-I R¹-IV X-II Y-I R¹-V X-II Y-I R¹-VI X-II Y-I R¹-VII X-II Y-I R¹-VIII X-II Y-I R¹-IX X-II Y-I R¹-X X-II Y-II R¹-X X-II Y-III R¹-X X-II Y-IV R¹-X X-II Y-V R¹-X X-II Y-VI R¹-I X-II Y-VI R¹-II X-II Y-VI R¹-III X-II Y-VI R¹-IV X-II Y-VI R¹-V X-II Y-VI R¹-VI X-II Y-VI R¹-VII X-II Y-VI R¹-VIII X-II Y-VI R¹-IX X-II Y-VI R¹-X X-III Y-I R¹-I X-III Y-I R¹-II X-III Y-I R¹-III X-III Y-I R¹-IV X-III Y-I R¹-V X-III Y-I R¹-VI X-III Y-I R¹-VII X-III Y-I R¹-VIII X-III Y-I R¹-IX X-III Y-I R¹-X X-III Y-I R¹-XI X-III Y-II R¹-X X-III Y-III R¹-X X-III Y-IV R¹-X X-III Y-V R¹-X X-III Y-VI R¹-I X-I Y-I R¹-XII X-I Y-I R¹-XIII X-I Y-I R¹-XIV X-I Y-I R¹-XV X-I Y-I R¹-XVI X-I Y-I R¹-XVII X-I Y-I R¹-XVIII X-III Y-I R¹-XII X-III Y-I R¹-XIII X-III Y-I R¹-XIV X-III Y-I R¹-XV X-III Y-I R¹-XVI X-III Y-I R¹-XVII X-III Y-I R¹-XVIII X-III Y-VI R¹-II X-III Y-VI R¹-III X-III Y-VI R¹-IV X-III Y-VI R¹-V X-III Y-VI R¹-VI X-III Y-VI R¹-VII X-III Y-VI R¹-VIII X-III Y-VI R¹-IX X-III Y-VI R¹-X X-III Y-VI R¹-XI X-IV Y-I R¹-I X-IV Y-I R¹-II X-IV Y-I R¹-III X-IV Y-I R¹-IV X-IV Y-I R¹-V X-IV Y-I R¹-VI X-IV Y-I R¹-VII X-IV Y-I R¹-VIII X-IV Y-I R¹-IX X-IV Y-I R¹-X X-IV Y-I R¹-XI X-IV Y-II R¹-X X-IV Y-III R¹-X X-IV Y-IV R¹-X X-IV Y-V R¹-X X-IV Y-VI R¹-I X-IV Y-VI R¹-II X-IV Y-VI R¹-III X-IV Y-VI R¹-IV X-IV Y-VI R¹-V X-IV Y-VI R¹-VI X-IV Y-VI R¹-VII X-IV Y-VI R¹-VIII X-IV Y-VI R¹-IX X-IV Y-VI R¹-X X-IV Y-VI R¹-XI X-V Y-I R¹-I X-V Y-I R¹-VII X-V Y-I R¹-IX X-V Y-I R¹-X X-V Y-II R¹-X X-V Y-III R¹-X X-V Y-IV R¹-X X-V Y-V R¹-X X-V Y-VI R¹-I X-V Y-VI R¹-VII X-V Y-VI R¹-IX X-V Y-VI R¹-X X-VI Y-I R¹-I X-VI Y-I R¹-II X-VI Y-I R¹-III X-VI Y-I R¹-IV X-VI Y-I R¹-V X-VI Y-I R¹-VI X-VI Y-I R¹-VII X-VI Y-I R¹-VIII X-VI Y-I R¹-IX X-VI Y-I R¹-X X-VI Y-II R¹-X X-VI Y-III R¹-X X-VI Y-IV R¹-X X-VI Y-V R¹-X X-VI Y-VI R¹-I X-VI Y-VI R¹-II X-VI Y-VI R¹-III X-VI Y-VI R¹-IV X-VI Y-VI R¹-V X-VI Y-VI R¹-VI X-VI Y-VI R¹-VII X-VI Y-VI R¹-VIII X-VI Y-VI R¹-IX X-VI Y-VI R¹-X X-VII Y-I R¹-I X-VII Y-I R¹-II X-VII Y-I R¹-III X-VII Y-I R¹-IV X-VII Y-I R¹-V X-VII Y-I R¹-VI X-VII Y-I R¹-VII X-VII Y-I R¹-VIII X-VII Y-I R¹-IX X-VII Y-I R¹-X X-VII Y-II R¹-X X-VII Y-III R¹-X X-VII Y-IV R¹-X X-VII Y-V R¹-X X-VII Y-VI R¹-I X-VII Y-VI R¹-II X-VII Y-VI R¹-III X-VII Y-VI R¹-IV X-VII Y-VI R¹-V X-VII Y-VI R¹-VI X-VII Y-VI R¹-VII X-VII Y-VI R¹-VIII X-VII Y-VI R¹-IX X-VII Y-VI R¹-X X-VIII Y-I R¹-X X-VIII Y-VI R¹-X X-IX Y-I R¹-X X-IX Y-VI R¹-X X-I Y-VI R¹-XII X-I Y-VI R¹-XIII X-I Y-VI R¹-XIV X-I Y-VI R¹-XV X-I Y-VI R¹-XVI X-I Y-VI R¹-XVII X-I Y-VI R¹-XVIII X-III Y-VI R¹-XII X-III Y-VI R¹-XIII X-III Y-VI R¹-XIV X-III Y-VI R¹-XV X-III Y-VI R¹-XVI X-III Y-VI R¹-XVII X-III Y-VI R¹-XVIII

The compounds of the present invention can be produced for example according to the methods mentioned below.

The compound of formula (I-1) wherein A¹, A², A³, G, X, Y, R¹, R², R³, m and n are as defined above that is the compound of formula (1) wherein W is oxygen atom can be obtained by reacting the compound of formula (5) wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above with the compound of formula (6) wherein R¹ and R² are as defined above by use of a condensation agent, optionally by using a solvent inactive for the reaction, optionally in the presence of a base.

The reaction substrates can be used in an amount of 1 to 100 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (5).

The condensation agent is not specifically limited if it is a compound used for ordinary amide synthesis, but it is for example Mukaiyama agent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexyl carbodiimide), WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole), dimethylpropynyl sulfonium bromide, propagyl triphenyl phosphonium bromide, DEPC (diethyl phosphorocyanidate) or the like, and can be used in an amount of 1 to 4 equivalents based on the compound of formula (5).

In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, acetonitrile and dimethyl sulfoxide, and the like. These solvents may be used alone or in a mixture of two or more.

The addition of a base is not necessarily required. However, when the base is used, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethylamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (5).

The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 20 equivalents of the compound of formula (6) and 1 to 4 equivalent of the condensation agent such as WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole) or the like based on 1 equivalent of the compound of formula (5), optionally in the presence of 1 to 4 equivalents of a base such as potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without solvent or in a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofurane, 1,4-dioxane or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.

In addition, the compound of formula (1-1) according to the present invention can be also synthesized by reacting the compound of formula (7) wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above, J¹ is chlorine atom, bromine atom, C₁-C₄alkylcarbonyloxy (for example pivaloyloxy), C₁-C₄alkoxycarbonyloxy (for example isobutyloxycarbonyloxy) or azolyl (for example imidazol-1-yl) that can be synthesized according to a known method disclosed in documents from the compound of formula (5), for example a method by reacting with a chlorinating agent such as thionyl chloride, phosphorus pentachloride or oxalyl chloride, a method by reacting with a organic acid halide such as pivaloyl chloride or isobutyl chlorformate, etc. optionally in the presence of a base, or a method by reacting with carbonyl diimidazole or sulfonyl diimidazole, etc., with the compound of formula (6), optionally by using a solvent inactive for the reaction, optionally in the presence of a base.

The reaction substrates can be used in an amount of 1 to 50 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (7).

In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, acetonitrile and water, and the like. These solvents may be used alone or in a mixture of two or more.

The addition of a base is not necessarily required. However, when the base is used, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethylamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (7).

The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (7), optionally in the presence of 1 to 2 equivalents of a base such as potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without solvent or in a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofurane, 1,4-dioxane, ethyl acetate, acetonitrile or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.

Hydroxamic chloride of formula (9) wherein A¹, A², A³, W, Y, R¹, R² and n are as defined above, J² means halogen atom such as chlorine atom and bromine atom can be obtained by halogenating the compound of formula (8) wherein A¹, A², A³, W, Y, R¹, R² and n are as defined above using a halogenating reagent optionally by using a solvent inactive for the reaction, optionally in the presence of a base.

Halogenating agents include for example N-halosuccinimides such as N-chlorosuccinimide, N-bromosuccinimide or the like, hypohalogenous acid alkali metal salts such as sodium hypochlorite or the like, hypohalogenous acid esters such as hypochlorous acid-t-butyl ester or the like, simple substance halogens such as chlorine gas or the like, and it can be used in an amount of 1 to 10 equivalents based on the compound of formula (8).

In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, alcohols such as methanol, ethanol, ethylene glycol or the like, carboxylic acids such as acetic acid, propionic acid or the like, acetonitrile and water, and the like. These solvents may be used alone or in a mixture of two or more.

The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 24 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.

The compounds of formula (1) wherein A¹, A², A³, G, W, X, Y, R¹, R², R³, m and n are as defined above according to the present invention can be obtained by reacting the compound of formula (9) with the compound of formula (10) wherein G, X, R³ and m are as defined above in the presence of a base optionally by use of a solvent inactive for the reaction.

The reaction substrates can be used in an amount of 1 to 5 equivalents of the compound of formula (10) based on 1 equivalent of the compound of formula (9).

The used base includes for example alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethylamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 5 equivalents based on the compound of formula (9).

In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, and acetonitrile, and the like. These solvents may be used alone or in a mixture of two or more.

The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.

Generally, the compound of formula (9) can be obtained for example by carrying out the reaction by using 1 to 2 equivalents of a halogenating agent such as N-chlorosuccinimide, sodium hypochlorite aqueous solution, hypochlorous acid-t-butyl ester, chlorine gas or the like based on 1 equivalent of the compound of formula (8) in a solvent such as dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, N,N-dimethylformamide or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 2 hours. Then, preferably without the isolation of the compound of formula (9), 1 to 2 equivalents of the compound of formula (10) and 1 to 2 equivalents of a base such as sodium carbonate, sodium hydrogen carbonate, triethyl amine or the like are added, and the reaction is carried out at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.

The compound of formula (1-1) wherein A¹, A², A³, G, X, Y, R¹, R³, m and n are as defined above and R² has the same meaning defined above excluding hydrogen atom according to the present invention that is the compound of formula (1) wherein W is oxygen atom can be obtained by reacting the compound of formula (1-2) wherein A¹, A², A³, G, X, Y, R¹, R³, m and n are as defined above that is the compound of formula (1) wherein W is oxygen atom and R² is hydrogen atom with the compound of formula (11) wherein R² has the same meaning defined above excluding hydrogen atom, J³ is a good leaving group such as chlorine atom, bromine atom, iodine atom, C₁-C₄alkylcarbonyloxy (for example pivaloyloxy), C₁-C₄alkylsulfonate (for example methane sulfonyloxy), C₁-C₄haloalkylsulfonate (for example trifluoromethane sulfonyloxy), arylsulfonate (for example benzene sulfonyloxy, p-toluene sulfonyloxy) or azolyl (for example imidazol-1-yl), optionally in the presence of a base, optionally by using a solvent inactive for the reaction.

The reaction substrates can be used in an amount of 1 to 50 equivalents of the compound of formula (11) based on 1 equivalent of the compound of formula (1-2).

In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, alcohols such as methanol, ethanol, ethylene glycol or the like, acetonitrile, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and water, and the like. These solvents may be used alone or in a mixture of two or more.

When the base is used, alkali metal hydride such as sodium hydride, potassium hydride or the like, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal alkoxides such as sodium ethoxide, potassium t-butoxide or the like, alkali metal amides such as lithium diisopropylamide, lithium hexamethyl disilazane, sodium amide or the like, organic metal compounds such as t-butyl lithium or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like, organic bases such as triethylamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (1-2).

The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of the compound of formula (11) based on 1 equivalent of the compound of formula (1-2), in a polar solvent such as tetrahydrofurane, 1,4-dioxane, acetonitrile, N,N-dimethylformamide or the like, optionally in the presence of 1 to 3 equivalents of a base such as sodium hydride, potassium t-butoxide, potassium hydroxide, potassium carbonate, triethylamine, pyridine or the like, based on 1 equivalent of the compound of formula (1-2), at a temperature ranging from 0 to 90° C. for 10 minutes to 24 hours.

The compound of formula (1-3) wherein A¹, A², A³, G, X, Y, R¹, R², R³, m and n are as defined above according to the present invention that is the compound of formula (1) wherein W is sulfur atom can be obtained by reacting the compound of formula (1-1) wherein A¹, A², A³, G, X, Y, R¹, R², R³, m and n are as defined above according to the present invention that is the compound of formula (1) wherein W is oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide), optionally by using a solvent inactive for the reaction, optionally in the presence of a base.

The reaction substrates can be used in an amount of 1 to 50 equivalents of the sulfurizing agent based on 1 equivalent of the compound of formula (1-1).

In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, and HMPA (hexamethylphosphoric triamide), and the like. These solvents may be used alone or in a mixture of two or more.

The addition of a base is not necessarily required. However, when the base is used, alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like, organic bases such as triethylamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 10 equivalents based on the compound of formula (1-1).

The reaction temperature may be an arbitrary temperature ranging from 0° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO, Lawesson's Reagent or the like, based on 1 equivalent of the compound of formula (1-1), optionally in the presence of 1 to 4 equivalents of a base such as sodium hydrogen carbonate, triethylamine, pyridine or the like, in a solvent such as benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, HMPA or the like, at a temperature ranging from room temperature to the reflux temperature of the reaction mixture for 10 minutes to 50 hours, or in a solvent amount of pyridine at a temperature of 80° C. to the reflux temperature of the reaction mixture for 1 to 3 hours.

In Production Method A to Production Method D, the aimed compound of the present invention can be obtained by subjecting the reaction mixture after the completion of the reaction to ordinary post-treatment such as a direct concentration, or a concentration after dissolving in an organic solvent and washing with water or a concentration after placing in ice water and extracting with an organic solvent. In addition, when a purification is required, it can be separated and purified by an arbitrary purification process such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatograph collection or the like.

The compound of formula (5) used in Production Method A can be synthesized as follows, for example.

That is, the compound of formula (5) wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above can be obtained by reacting the compound of formula (12) wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above, J⁴ is bromine atom, iodine atom, halosulfonyloxy (for example fluorosulfonyloxy), C₁-C₄haloalkylsulfonyloxy (for example trifluoromethane sulfonyloxy) or arylsulfonyloxy (for example benzenesulfonyloxy) according to a known method disclosed in documents, for example by CO insertion reaction by use of a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1999, vol. 64, p. 6921 or the like, or by a process by lithiation and then reaction with carbonic acid gas stated in Chem. Rev., 1990, vol. 90, p. 879.

In addition, the compound of formula (5) can be obtained by subjecting the compound of formula (12) to a reaction according to a reaction condition for CO insertion reaction by use of a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1974, vol. 39, p. 3318 or the like to convert the compound of formula (13) wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above, R^(b) is C₁-C₆alkyl such as methyl, ethyl or the like, and then hydrolizing according to an ordinary ester hydrolysis disclosed in documents, for example a reaction condition stated in Angew. Chem., 1951, vol. 63, p. 329, J. Am. Chem. Soc., 1929, vol. 51, p. 1865 or the like.

Some of the compounds of formula (6) used in Production Method A are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be synthesized according to methods stated in for example Justus Liebigs Ann. Chem., 1979, p. 920, U.S. Pat. No. 5,990,323, WO 96/11200 or the like, and general synthetic methods for primary or secondary alkyl amines disclosed in documents.

The compounds of formula (8) used in Production Method B can be synthesized as follows, for example.

That is, the compound of formula (8) wherein A¹, A², A³, W, Y, R¹, R² and n are as defined above can be easily synthesized by reacting the compound of formula (14) wherein A¹, A², A³, W, Y, R¹, R² and n are as defined above with hydroxyamine or the salt thereof according to known methods disclosed in documents, for example the method stated in J. Med. Chem., 2001, vol. 44, p. 2308 or the like.

The compounds of formula (10) used in Production Method B can be synthesized as follows, for example.

That is, the compound of formula (10) wherein G, X, R³ and m are as defined above can be obtained by reacting the known compound of formula (15) wherein G, X and m are as defined above, J⁵ is bromine atom, iodine atom, C₁-C₄haloalkylsulfonyloxy (for example trifluoromethanesulfonyloxy), —B(OH)₂, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, —Si(OEt)₃, —ZnCl, —ZnBr or —ZnI, etc. with the compound of formula (16) wherein R³ is as defined above, J⁶ is halogen atom such as bromine atom, iodine atom or the like, or —B(OH)₂ according to an ordinary crosscoupling reaction by use of a transition metal catalyst such as palladium or the like disclosed in documents, for example a reaction condition stated in J. Org. Chem., 1991, vol. 56, p. 7336, Tetrahedron Lett., 2001, vol. 42, p. 4083, or the like.

Some of the compounds of formula (16) used in the above-mentioned process are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be synthesized according to methods disclosed in documents, for example a method stated in J. Am. Chem. Soc., 1971, vol. 93, p. 1925, Tetrahedron Lett., 1990, vol. 31, p. 1919 and 2001, vol. 42, p. 4083 or the like.

In addition, the compounds of formula (10) can be obtained by reacting the compound of formula (17) wherein G, X, R³ and m are as defined above according to a reaction of converting carbonyl to olefine disclosed in documents, for example a reaction condition stated in J. Org. Chem., 1986, vol. 51, p. 5252 and 1994, vol. 59, p. 2898, Synthesis, 1991, p. 29, Tetrahedron Lett., 1985, vol. 26, p. 5579 or the like.

Some of the compounds of formula (11) used in Production method C are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be easily synthesized according to methods disclosed in documents, for example a method stated in Chem. Lett., 1976, p. 373, J. Am. Chem. Soc., 1964, vol. 86, p. 4383, J. Org. Chem., 1976, vol. 41, p. 4028 and 1978, vol. 43, p. 3244, Org. Synth., 1988, Corrective vol. 6, p. 101, Tetrahedron Lett., 1972, p. 4339, GB 2,161,802, EP 0,051,273 or the like.

The compounds of formula (12) can be synthesized as follows, for example.

That is, the compounds of formula (12) wherein A¹, A², A³, G, X, Y, R³, m, n and J⁴ are as defined above can be obtained by halogenating the compound of formula (18) wherein A¹, A², A³, Y, n and J⁴ are as defined above under a condition similar to that of Production Method B to obtain the compound of formula (19) wherein A¹, A², A³, Y, n, J³ and J⁴ are as defined above, and then reacting it with the compound of formula (10) wherein G, X, R³ and m are as defined above.

The compound of formula (18) can be easily synthesized by use of the corresponding known substituted aromatic aldehyde similarly to the process described in Reaction Scheme 2.

The compound of formula (14) can be synthesized for example according to Reaction Scheme 5 or Reaction Scheme 6.

The compounds of formula (14) wherein A¹, A², A³, W, Y, R¹, R² and n are as defined above can be obtained by subjecting the compound of formula (20) wherein A¹, A², A³, W, Y, R¹, R², n and J⁴ are as defined above to CO insertion reaction according to known methods disclosed in documents, for example the reaction by use of a transition metal catalyst such as palladium or the like in the presence of hydride source such as formic acid or the like stated in Bull. Chem. Soc. Jpn., 1994, vol. 67, p. 2329, J. Am. Chem. Soc., 1986, vol. 108, p. 452, or the like.

The compounds of formula (14-1) wherein A¹, A², A³, Y, R¹, R² and n are as defined above that are the compounds of formula (14) wherein W is oxygen atom can be synthesized by reacting the known compound of formula (21) wherein A¹, A², A³, Y and n are as defined above with the compound of formula (6) wherein R¹ and R² are as defined above by use of the method similar to Production Method A.

The compounds of formula (17) can be synthesized as follows, for example.

That is, the compounds of formula (17) wherein X, R³ and m are as defined above, G is benzene ring can be obtained by reacting the known compound of formula (23) wherein X and m are as defined above, G is benzene ring with the known compound of formula (24) wherein R³ is as defined above, J⁷ is a leaving group such as halogen atom, trifluoromethanesulfonyloxy, 2-pyridyloxy or the like, or the known compound of formula (25) wherein R³ is as defined above according to a general acylating reaction of aromatic ring disclosed in documents, for example a method stated in Chem. Lett., 1990, p. 783, J. Org. Chem., 1991, vol. 56, p. 1963 or the like.

In addition, the compound of formula (17) wherein G, X, R³ and m are as defined above can be obtained according to general methods disclosed in documents for example by a method stated in J. Am. Chem. Soc., 1955, vol. 77, p. 3657, Tetrahedron Lett., 1980, vol. 21, p. 2129 and 1991, vol. 32, p. 2003, U.S. Pat. No. 5,514,816 in which the compound of formula (26) wherein G, X and m are as defined above, J⁸ is bromine atom or iodine atom is lithiated and the resulting compound is reacted with the known compound of formula (27) wherein R³ is as defined above, J⁹ is halogen atom, hydroxy, metal salt (for example, —OLi, —ONa), C₁-C₄alkoxy (for example, methoxy, ethoxy), di(C₁-C₄alkyl)amino (for example, diethylamino), C₁-C₄alkoxy C₁-C₄alkyl amino(for example O,N-dimethylhydroxyamino) or cyclic amino (for example, piperidin-1-yl, morpholin-4-yl, 4-methylpiperidin-1-yl), or the known compound of formula (25), or by a method stated in Heterocycles, 1987, vol. 25, p. 221, Synth. Commun., 1985, vol. 15, p. 1291 and 1990, vol. 20, p. 1469, DE 19727042, or the like in which a Grignard reagent is formed and then it is reacted with the compound of formula (27) or the compound of formula (25).

The compounds of formula (20) can be synthesized according to for example Reaction Scheme 8 or Reaction Scheme 9.

The compounds of formula (20-1) wherein A¹, A², A³, Y, R¹, R², n and J⁴ are as defined above that are the compounds of formula (20) wherein W is oxygen atom can be obtained by reacting the known compound of formula (28) wherein A¹, A², A³, Y, n and J⁴ are as defined above with the compound of formula (6) wherein R¹ and R² are as defined above by use of the method similar to Production Method A.

The compounds of formula (20-2) wherein A¹, A², A³, Y, R¹, R², n and J⁵ are as defined above that are the compounds of formula (20) wherein W is sulfur atom can be obtained by reacting the compound of formula (20-1) wherein A¹, A², A³, Y, R¹, R², n and J⁴ are as defined above that are the compounds of formula (20) wherein W is oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide) under a condition similar to that of Production Method D.

In each reaction, after the completion of the reaction, each production intermediate that is a starting compound in Production Method A to Production Method C can be obtained by carrying out normal post-treatments.

In addition, each production intermediate produced by the above-mentioned methods can be used for the following reaction step as such without isolation or purification.

The active compounds included in the present invention concretely include for example the compounds shown in Tables 2 and 3. The compounds that can be used as novel production intermediates for producing the active compounds included in the present invention concretely include for example the compounds shown in Tables 4 to 6. In the interim, the compounds shown in Tables 2 to 6 are for purposes of illustration and the present invention is not limited thereto.

In the meantime, in Tables, the indication “Et” means ethyl, hereinafter similarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and “Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and “Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu” and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu” and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” mean normal pentyl, “c-Pen” and “Pen-c” mean cyclopentyl, “n-Hex” and “Hex-n” mean normal hexyl, “c-Hex” and “Hex-c” mean cyclohexyl, “Hept” means heptyl, “Oct” means octyl, “Ph” means phenyl, “1-Naph” means 1-naphthyl, “2-Naph” means 2-naphthyl, and in Tables, aromatic heterocyclic rings of D-1a to D-65a are the following structures, respectively

For example, the indication “[CH₂(D-17a)CH₃]” means 1-methylpyrazol-5-yl methyl, the indication “[CH₂(D-22b)CH₃] means 2-methylthiazol-4-yl methyl.

In addition, aliphatic heterocyclic rings of E-4-a to E-43b are the following structures, respectively

For example, the indication “[CH₂(E-10b)CH₃]” means 2-methyl-1,3-dioxolan-2-yl methyl, the indication “[CH₂(E-8a)CH₃]” means N-methylpyrrolidin-2-yl methyl. Further, in Tables, partially saturated heterocyclic rings of M-2a to M-16a are the following structures, respectively

For example, the indication “[CH₂(M-5a)CH₃]” means 3-methyl-4,5-dihydroisoxazole-5-yl methyl.

Further, in Tables, T-1 to T-49 are the following structures, respectively

Lengthy table referenced here US20090312330A1-20091217-T00001 Please refer to the end of the specification for access instructions.

Lengthy table referenced here US20090312330A1-20091217-T00002 Please refer to the end of the specification for access instructions.

Lengthy table referenced here US20090312330A1-20091217-T00003 Please refer to the end of the specification for access instructions.

Lengthy table referenced here US20090312330A1-20091217-T00004 Please refer to the end of the specification for access instructions.

Lengthy table referenced here US20090312330A1-20091217-T00005 Please refer to the end of the specification for access instructions.

The compounds of the present invention can effectively control in a low concentration so-called agricultural insects injuring agricultural and horticultural crops and trees, so-called domestic animal pests parasitizing domestic animals and domestic fowls, so-called hygienic pests having an adverse affect on human being's environment such as houses, insects as so-called stored grain insects injuring grains and the like stored in storehouses, and any pests of acarids, crustaceans, mollusks and nematodes generating in the similar scenes.

The insects, acarids, crustaceans, mollusks and nematodes that the compounds of the present invention can control concretely include for example the followings:

Lepidoptera insects, such as Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Archips fuscocupreanus, Grapholita molesta, Homona magnanima, Leguminivora glycinivorella, Matsumuraeses phaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Lyonetia prunifoliella malinella, Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda masinissa, Helcystogramma triannulella, Pectinophora gossypiella, Carposina sasakii, Cydla pomonella, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diaphania indica, Etiella zinckenella, Glyphodes pyloalis, Hellula undalis, Ostrinia furnacalis, Ostrinia scapulalis, Ostrinia nubilalis, Parapediasia teterrella, Parnara guttata, Pieris brassicae, Pieris rapae crucivora, Ascotis selenaria, Pseudoplusia includens, Euproctis pseudoconspersa, Lymantria dispar, Orgyia thyellina, Hyphantria cunea, Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Mamestra brassicae, Mythimna separata, Naranga aenescens, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera depravata, Trichoplusia ni, Endopiza viteana, Manduca quinquemaculata, Manduca sexta, or the like; Thysanoptera insects, such as Frankliniella intonsa, Frankliniella occidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Ponticulothrips diospyrosi, or the like; Hemiptera insects, such as Dolycoris baccarum, Eurydema rugosum, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glaucias subpunctatus, Halyomorpha halys, Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia crossota, Scotinophora lurida, Cletus punctiger, Leptocorisa chinensis, Riptortus clavatus, Rhopalus msculatus, Cavelerius saccharivorus, Togo hemipterus, Dysdercus cingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium, Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Macrosteles striifrons, Nephotettix cinctinceps, Psuedatomoscelis seriatus, Laodelphax striatella, Nilaparvata lugens, Sogatella furcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, Viteus vitifolii, Aphis gossypii, Aphis spiraecola, Myzus persicae, Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Planococcus citri, Planococcus kuraunhiae, Pseudococcus comstocki, Ceroplastes ceriferus, Ceroplastes rubens, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis euonymi, Unaspis yanonensis, Cimex lectularius, or the like; Coleoptera insects, such as Anomala cuprea, Anomala rufocuprea, Gametis jucunda, Heptophylla picea, Popillia japonica, Lepinotarsa decemlineata, Melanotus fortnumi, Melanotus tamsuyensis, Lasioderma serricorne, Epuraea domina, Epilachna varivestis, Epilachna vigintioctopunctata, Tenebrio molitor, Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchus chinensis, Aulacophora femoralis, Chaetocnema concinna, Diabrotica undecimpunctata, Diabrotica virgifera, Diabrotica barberi, Oulema oryzae, Phyllotreta striolata, Psylliodes angusticollis, Rhynchites heros, Cylas formicarius, Anthonomus grandis, Echinocnemus squameus, Euscepes postfasciatus, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus vestitus, Paederus fuscipes, or the like; Diptera insects, such as Asphondylia yushimai, Sitodiplosis mosellana, Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis capitata, Hydrellia griseola, Drosophila suzukii, Agromyza oryzae, Chromatomyia horticola, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii, Delia platura, Pegomya cunicularia, Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans, Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanus trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens, Aedes aegypti, Aedes albopicutus, Anopheles hyracanus sinesis, or the like; Hymenoptera insects, such as Apethymus kuri, Athalia rosae, Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti, Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp., Monomorium pharaonis, or the like; Orthoptera insects, such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis, Schistocerca gregaria, or the like; Collembola insects, such as Onychiurus folsomi, Onychiurus sibiricus, Bourletiella hortensis, or the like; Dictyoptera insect, such as Periplaneta fuliginosa, Periplaneta japonica, Blattella germanica, or the like; Isoptera insects, such as Coptotermes formosanus, Reticulitermes speratus, Odontotermes formosanus, or the like; Siphonaptera insects, such as Ctenocephalidae felis, Ctenocephalides canis, Echidnophaga gallinacea, Pulex irritans, Xenopsylla cheopis, or the like; Mallophaga insects, such as Menacanthus stramineus, Bovicola bovis, or the like; Anoplura insects, such as Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Solenopotes capillatus, or the like; Tarsonemid mites, such as Phytonemus pallidus, Polyphagotarsonemus latus, Tarsonemus bilobatus, or the like; Eupodid mites, such as Penthaleus erythrocephalus, Penthaleus major, or the like; Spider mites, such as Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai, Tetranychus urticae, or the like; Eriophyid mites, such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis, Phyllocoptruta oleivora, or the like; Acarid mites, such as Rhizoglyphus robini, Tyrophagus putrescentiae, Tyrophagus similis, or the like; Bee brood mites, such as Varroa jacobsoni, or thelike; Ixodides, such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemophysalis flava, Haemophysalis campanulata, Ixodes ovatus, Ixodes persulcatus, Amblyomma spp., Dermacentor spp., or the like; Cheyletidae, such as Cheyletiella yasguri, Cheyletiella blakei, or the like; Demodicidae, such as Demodex canis, Demodex cati, or the like; Psoroptidae, such as Psoroptes ovis, or the like; Scarcoptidae, such as Sarcoptes scabiei, Notoedres cati, Knemidocoptes spp., or the like; Crustacea, such as Armadillidium vulgare, or the like; Gastropoda, such as Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Limax Valentiana, Acusta despecta sieboldiana, Euhadra peliomphala, or the like; Nematodes, such as Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi, Bursaphelenchus xylophilus, or the like. But the present invention is not limited thereto.

The endo-parasites of domestic animals, domestic fowls, pets and the like that the compounds of the present invention can control concretely include for example the followings:

Nematodes, such as Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, or the like; Filariidae in nematodes, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa, or the like; Dracunculidae in nematodes, such as Deacunculus, or the like; Cestoda, such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis, or the like; Trematoda, such as Fasciola hepatica, F. gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni, or the like; Eimeria spp., such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria ovinoidalis, or the like; Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., or the like. But the present invention is not limited thereto.

Further, the compounds of the present invention are effective for pests acquiring high resistance against existing insecticides such as organic phosphorus compounds, carbamate compounds or pyrethroid compounds, etc.

That is, the compounds of the present invention can effectively control pests that belong to insects such as Collembola, Dictyoptera, Orthoptera, Isoptera, Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera and Anoplura, Acarina, Gastropoda and Nematoda, in a low concentration. On the other hand, the compounds of the present invention have an extremely useful charactristic that they have little adverse affect on mammals, fishes, crustaceans and useful insects (beneficial insect such as honeybee, bumblebee or the like, or, natural enemies such as Aphytis lingnanensis, Aphidius colemani, Orius strigicollis, Amblyseius californicus, or the like).

When the compounds of the present invention are used, they can be generally mixed with a suitable solid carrier or liquid carrier, optionally along with surfactant, penetrating agent, spreading agent, thickner, anti-freezing agent, binder, anti-caking agent, disintegrating agent, anti-foaming agent, preservative, stabilizer, and the like, and can be formulated into any desired forms for practical use, such as soluble concentrates, emulsifiable concentrates, wettable powders, water soluble powders, water dispersible granules, water soluble granules, suspension concentrates, concentrated emulsions, suspoemulsions, microemulsions, dustable powders, granules, tablets and emulsifiable gels. From the viewpoint of an elimination or reduction of labor and an improvement of safety, the formulations in any desired forms described above may be included into a water-soluble bag made of water-soluble capsule or water-soluble film.

The solid carrier includes, for example, natural minerals such as quartz, calcite, sepiolite, dolomaite, chalk, kaolinite, pyrofilite, celicite, halocite, methahalocite, kibushi clay, gairome clay, pottery stone, zeaklite, allophane, white sand, mica, talc, bentonite, activeted earth, acid china clay, pumice, attapulgite, zeolite and diatomaceous earth, etc., calcined products of natural minerals such as calcined clay, perlite, white sand balloon (loam balloon), vermiculite, attapulgus clay and calcined diatomaceous earth, etc., inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, etc., saccharides such as glucose, fructose, sucrose and lactose, etc., polysaccharides such as starch, powder cellulose and dextrin, etc., organic materials such as urea, urea derivatives, benzoic acid and a salt of benzoic acid, etc., plants such as wood powder, cork powder, corn head stem, walnut shell and tobacco stem, etc., fly ash, white carbon (e.g., hydrated synthetic silica, anhydrous synthetic silica and hydrated synthetic silicate, etc.) and fertilizers, etc.

As the liquid carrier, there may be mentioned, for example, aromatic hydrocarbons such as xylene, alkyl(C₉ or C₁₀, etc.)benzene, phenylxylylethane and alkyl(C₁ or C₃, etc.)naphthalene, etc., aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin and naphthene, etc., a mixture of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene, etc., alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzylalcohol, etc., polyvalent alcohols such as ethylene glycol, propyleneglycol, diethylene glycol, hexylene glycol, polyethylene glycol and polypropyleneglycol, etc., ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propyleneglycol monomethyl ether, propyleneglycol monoethyl ether, propyleneglycol monopropyl ether, propyleneglycol monobutyl ether and propyleneglycol monophenyl ether, etc., ketones such as acetophenone, cyclohexanone and -butyrolactone, etc., esters such as aliphatic acid methyl ester, dialkyl succinate, dialkyl glutamate, dialkyl adipate and dialkyl phthalate, etc., acid amides such as N-alkyl(C₁, C₈ or C₁₂, etc.) pyrrolidone, etc., oil and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and caster oil, etc., dimethylsulfoxide and water.

These solid and liquid carriers may be used alone or in combination of two or more kinds in combination.

As the surfactant, there may be mentioned, for example, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono- or di-)phenyl ether, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid (mono- or di-)ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, caster oil-ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol and alkyl glycoside, etc., anionic surfactants such as alkyl sulfate, alkylbenzenesulfonate, lignine sulfonate, alkylsulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfonate, formalin condensate salt of naphthalene sulfonic acid, formalin condensate salt of alkylnaphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate, polyoxyethylene (mono- or di-)alkylphenyl ether sulfate or phosphate, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether sulfate or phosphate, polycarboxylate (e.g., polyacrylates, polymaleates and copolymer materials of maleic acid and olefin, etc.) and polystyrenesulfonate, etc., cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, etc., amphoteric surfactants such as amino acid type and betaine type, etc., silicone type surfactants and fluorine type surfactants.

A content of these surfactants is not specifically limited, and it is desirably in the range of 0.05 to 20 parts by weight in general based on 100 parts by weight of the preparation according to the present invention. Also, these surfactants may be used alone or in combination of two or more kinds in combination.

A dose of the compound of the present invention to be applied may vary depending on the place to be applied, time to be applied, method to be applied, crops to cultivate, etc., and in general, it is suitable in an amount of about 0.005 to 50 kg or so per a hectare (ha) as an amount of the effective ingredient.

On the other hand, when the compound of the present invention is used for controlling ecto- or endo-parasites of mammals and birds as domestic animals and pets, the effective amount of the compound of the present invention together with additives for formulations can be administered through oral administration, parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or the like; transdermal administration such as dipping, spray, bathing, washing, pouring-on and spotting-on, and dusting, or the like; transnasal administration. The compound of the present invention can be also administered through a formed product by use of a strip, a plate, a band, a collar, an ear mark, a limb band, a labe apparatus, or the like. In administration, the compound of the present invention can be formed in an arbitrary dosage form that is suited for the administration route.

The arbitrary dosage form includes solid preparations such as a dustable powder, a granule, wettable powder, a pellete, a tablet, a bolus, a capsule, a formed product containing an active compound; liquid formulations such as an injectable liquid formulation, an oral liquid formulation, a liquid formulation used on skin or in body cavity; solution preparations such as a pour-on agent, a spot-on agent, a flowable agent, an emulsifiable concentrate; semi-solid preparations such as an ointment, gel or the like.

The solid preparations can be mainly used through oral administration or transdermal administration by diluting with water or the like, or by environmental treatment. The solid preparations can be prepared by mixing the active compound with suitable excipients and optionally auxiliary substances and converting to a desired form. The suitable excipients include for example inorganic substances such as carbonates, hydrogen carbonates, phosphates, aluminum oxide, silica, clay or the like, organic substances such as sugar, cellulose, milled cereal, starch or the like.

The injectable liquid formulation can be administered intravenously, intramuscularly and subcutaneously. The injectable liquid formulation can be prepared by dissolving an active compound in a suitable solvent and optionally by adding an additive such as a solubilizing agent, an acid, a base, a buffering salt, an antioxidant, and a protective agent or the like. Suitable solvent is for example water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, poethylene glycol, N-methylpyrrolidone, and a mixture thereof, a physiologically permissible vegetable oil, a synthetic oil suitable for injection, or the like. The solubilizing agent includes polyvinyl pyrrolidone, polyoxyethylated castor oil and polyoxyethylated sorbitan ester, or the like. The protective agent includes benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester and n-butanol or the like.

The oral liquid formulation can be administered directly or after dilution. It can be prepared similarly to the injectable liquid formulation.

The flowable agent and the emulsifiable concentrate can be administered directly or after dilution through transdermal administration or environmental treatment.

The liquid formulation used on skin can be administered by pouring on, spreading, rubbing, atomizing, spraying, or dipping (dipping, bathing or washing). These liquid can be prepared similarly to the injectable liquid formulation.

The pour-on agent and the spot-on agent are poured or atomized on the limited spot on the skin, thereby the active compound can be penetrated into the skin and act in the whole body. The pour-on agent and the spot-on agent can be prepared by dissolving, suspending or emulsifying an active ingredient in a suitable skin-fitted solvent or solvent mixture. If required, an auxiliary substance such as a surfactant, a colorant, an absorption promoting agent, an antioxidant, a light stabilizer and an adhesive, etc. may be added.

Suitable solvent includes water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbon, vegetable or synthetic oil, DMF, liquid paraffin, light-duty liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane. The absorption promoting agent includes DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic ester, triglyceride and fatty alcohol. The antioxidant includes sulfite, metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.

The emulsifiable concentrate can be administrated orally, subcutaneously or injectably. The emulsifiable concentrate can be prepared by dissolving an active ingredient in a hydrophobic phase or a hydrophilic phase, and then homogenating the resulting solution with a suitable emulsifying agent optionally with further an auxiliary substance such as a colorant, an absorption promoting agent, a protective agent, an antioxidant, a light screen and a thickening agent.

The hydrophobic phase (oil) includes paraffin oil, silicone oil, sesame-seed oil, oil of almonds, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, ester of branched short chain length aliphatic acid with saturated aliphatic acid of chain length C16 to C18, isopropyl myristate, isopropyl palmitate, capryl/caprylic acid ester of saturated fatty alcohol of chain length C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, wax-like fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.

The hydrophilic phase includes water, propylene glycol, glycerin, sorbitol.

The emulsifying agent includes non-ionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan mono-olefinate, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; amphoteric surfactants such as di-sodium N-lauryl-iminodipropionate, lecithin or the like; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfuric acid ether, monoethanol amine salt of mono/dialkylpolyglycol orthophosphate or the like; cationic surfactants such as cetyl chloride trimethylammonium or the like.

The other auxiliary substance includes carboxymethylcellulose, methylcellulose, polyacrylate, arginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methylvinyl ether, copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica.

The semi-solid preparation can be administered by coating or spreading on the skin, or by introducing in body cavity. The gel can be prepared by adding a thickener in an amount enough to provide a clear substance having a viscosity of ointment in a solution prepared for the injectable liquid formulation as mentioned above.

Next, formulation examples of the preparation in case where the compound of the present invention is used are shown below. Provided that formulation examples of the present invention are not limited only thereto. In the interim, in the following Formulation Examples, “part(s)” mean part(s) by weight.

(Wettable Powder)

Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts As other components, there may be mentioned, for example, a non-caking agent, a decomposition preventing agent, and the like.

(Emulsifiable Concentrate)

Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts As other components, there may be mentioned, for example, a spreading agent, a decomposition preventing agent, and the like.

(Suspension Concentrate)

Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts As other components, there may be mentioned, for example, an antifreezing agent, a thickening agent, and the like.

(Water Dispersible Granule)

Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts As other components, there may be mentioned, for example, a binder, a decomposition preventing agent, and the like.

(Soluble Concentrate)

Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts As other components, there may be mentioned, for example, an antifreezing agent, a spreading agent, and the like.

(Granule)

Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts As other components, there may be mentioned, for example, a binder, a decomposition preventing agent, and the like.

(Dustable Powder)

Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts As other components, there may be mentioned, for example, a drift preventing agent, a decomposition preventing agent, and the like.

Next, formulation examples using the compound of the present invention as an effective ingredient are described in more detail, but the present invention is not limited thereto. In the interim, in the following Formulation Examples, “part(s)” mean part(s) by weight.

Formulation Example 1 Wettable Powder

Compound of the present invention No. 5-075 20 parts Pyrophylite 74 parts Solpol 5039  4 parts (A mixture of a nonionic surfactant and an anionic surfactant: available from TOHO Chemical Industry Co., LTD, Tradename) CARPREX #80D  2 parts (Synthetic hydrated silicic acid: available from Shionogi & Co., Ltd., Tradename) The above materials are uniformly mixed and pulverized to make wettable powder.

Formulation Example 2 Emulsion

Compound of the present invention No. 5-075  5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680  5 parts (A mixture of a nonionic surfactant and an anionic surfactant: available from TOHO Chemical Industry Co., LTD, Tradename) The above materials are uniformly mixed to make emulsifiable concentrate.

Formulation Example 3 Suspension Concentrate

Compound of the present invention No. 5-075 25 parts Agrisol S-710 10 parts (a nonionic surfactant: available from KAO CORPORATION, Tradename) Lunox 1000C 0.5 part (an anionic surfactant: available from TOHO Chemical Industry Co., LTD, Tradename) Xanthan gum 0.2 part Water 64.3 parts The above materials are uniformly mixed, and then, wet pulverized to make suspension concentrate.

Formulation Example 4 Water Dispersible Granule

Compound of the present invention No. 5-075 75 parts HITENOL NE-15  5 parts (an anionic surfactant: available from DAI-ICHI KOGYO SEIYAKU CO., LTD., Tradename) VANILLEX N 10 parts (an anionic surfactant: available from Nippon Paper Chemicals Co., Ltd., Tradename) CARPREX #80D 10 parts (Synthetic hydrated silicic acid: available from Shionogi & Co., Ltd., Tradename) The above materials are uniformly mixed and pulverized, and then, a small amount of water is added to the mixture and the resulting mixture is mixed under stirring, granulated by an extrusion granulator, and dried to make water dispersible granule.

Formulation Example 5 Granule

Compound of the present invention No. 5-075  5 parts Bentonite 50 parts Talc 45 parts The above materials are uniformly mixed and pulverized, and then, a small amount of water is added to the mixture and the resulting mixture is mixed under stirring, granulated by an extrusion granulator, and dried to make granule.

Formulation Example 6 Dustable Powder

Compound of the present invention No. 5-075 3 parts CARPREX #80D 0.5 parts (Synthetic hydrated silicic acid: available from Shionogi & Co., Ltd., Tradename) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above materials are uniformly mixed and pulverized to make dustable powder. When the formulation is used, it is sprayed by diluting with water in 1- to 1000-fold concentration, or directly without dilution.

Formulation Example 7 Wettable Powder Preparation

Compound of the present invention No. 5-086 25 parts Sodium diisobutylnaphthalenesulfonate 1 part Calcium n-dodecylbenzenesulfonate 10 parts Alkylaryl polyglycol ether 12 parts Sodium salt of naphthalenesulfonic acid formalin condensate 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaoline 45 parts

Formulation Example 8 Water-Soluble Concentrate Preparation

Compound of the present invention No. 5-086 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctylsulfosuccinate 3.5 parts Dimethylsulfoxide 37 parts 2-Propanol 36.5 parts

Formulation Example 9 Liquid Formulation for Atomization

Compound of the present invention No. 5-086  2 parts Dimethylsulfoxide 10 parts 2-Propanol 35 parts Acetone 53 parts

Formulation Example 10 Liquid Formulation for Transdermal Administration

Compound of the present invention No. 5-086  5 parts Hexylene glycol 50 parts Isopropanol 45 parts

Formulation Example 11 Liquid Formulation for Transdermal Administration

Compound of the present invention No. 5-086  5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts

Formulation Example 12 Liquid Formulation for Transdermal Administration (Pouring-on)

Compound of the present invention No. 5-086  2 parts Light-duty liquid paraffin 98 parts

Formulation Example 13 Liquid Formulation for Transdermal Administration (Pouring-on)

Compound of the present invention No. 5-086 2 parts Light-duty liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shinetsu silicone 1 part

Also, when the compound of the present invention is used as an agricultural chemicals, it may be mixed with other kinds of herbicides, various kinds of insecticides, acaricides, nematocides, fungicides, vegetable growth regulators, synergists, fertilizers, soil improvers, etc., and applied, at the time of preparing the formulation or at the time of spreading, if necessary.

In particular, by mixing with the other agricultural chemicals or plant hormones and applying the mixture, it can be expected that a cost is reduced due to reduction in a dose to be applied, enlargement in insecticidal spectrum or higher prevention and extinction effect of noxious organisms due to synergistic effect by mixing agricultural chemicals. At this time, it is possible to use the compound with a plural number of the conventionally known agricultural chemicals in combination simultaneously. As the kinds of the agricultural chemicals to be used in admixture with the compound of the present invention, there may be mentioned, for example, the compounds described in Farm Chemicals Handbook, 1999 ed. and the like. Specific examples of the general names can be enumerated below, but the invention is not necessarily limited only thereto.

Fungicides: acibenzolar-S-methyl, acylaminobenzamide, amobam, ampropyfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benthiazole, benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, carboxin, CGA-279202 (test name), chinomethionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, dazomet, debacarb, dichlorophen, diclobutrazol, dichlorfluanid, diclomedine, dicloran, diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenamidone, fendazosulam, fenfuram, fenhexamid, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, metiram, metominostrobin, myclobutanil, MTF-753 (test name), nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, NNF-9425 (test name), octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinomethionate, quinoxyfen, quintozene, RH 7281 (test name), sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole, thiadiazin/milneb, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zinc sulfate, zineb, ziram, and shiitake mushroom hyphae extract, etc.; Bactericides: streptomycin, tecloftalam, oxyterracycline, and oxolinic acid, etc.; Nematocides: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl, and fenamiphos, etc.; Acaricides: acequinocyl, amitraz, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, and tebufenpyrad, etc.; Insecticides: abamectin, acephate, acetamipirid, aldicarb, allethrin, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, fluacrypyrim, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nidinotefuran, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, protrifenbute, pymetrozine, pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, and vamidothion, etc.

Examples

Hereinafter, the present invention will be explained in more detail by specifically referring to Synthetic Examples and Test Examples of the compound of the present invention as working examples to which the present invention is not limited.

Synthetic Examples Synthetic Example 1 Production of the Compound of the Present Invention by Use of L-COS Parallel Liquid-Phase Synthesis System of MORITEX Corporation

In 15 bials of L-COS in which stirrers were placed, 1.5 mmol of each n-propylamine, i-propylamine, s-butylamine, t-butylamine, n-pentylamine, 2,2-dimethylpropylamine, n-hexylamine, cyclohexylamine, benzylamine, 4-trifluoromethylbenzylamine, 1-phenylethylamine, 2-phenylethylamine, 2-(4-phenoxyphenyl)ethylamine, 3-phenylpropylamine and trans-2-phenylcyclopropylamine was weighed, each bial was covered and placed in a reaction vessel of L-COS. With stirring at room temperature, in each bial, 5 ml of a solution of 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid in N,N-dimethylformamide-chloroform (1:3) (0.2 mmol/ml), 1 ml of a solution of 4-(dimethylamino)pyridine in chloroform (0.25 mmol/ml), and then 1.5 ml of a solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride in chloroform (1.0 mmol/ml) were added in that order, and continued to stir at the same temperature for 16 hours. After the completion of the reaction, 3 ml of cold water was added in each bials, and the organic phases were collected, and subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product was obtained as white to yellow solid. In addition, the product was confirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysis condition: 254 nm, 80% CH₃CN-20% H₂O-0.1% HCOOH, ionization: positive electrospray).

-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-n-propylbenzoic     acid amide; 0.26 g, [M⁺+H]=444.94. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-1-propylbenzoic     acid amide; 0.23 g, [M⁺+H]=444.94. -   N-s-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.20 g, [M⁺+H]=458.93. -   N-t-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.21 g, [M⁺+H]=458.92. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-n-pentylbenzoic     acid amide; 0.31 g, [M⁺+H]=473.02. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2-dimethyl     propyl)benzoic acid amide; 0.27 g, [M⁺+H]=472.94. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-n-hexylbenzoic     acid amide; 0.26 g, [M⁺+H]=486.96. -   N-cyclohexyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.26 g, [M⁺+H]=484.93. -   N-benzyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.34 g, [M⁺+H]=492.86. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(4-trifluoromethylbenzyl)benzoic     acid amide; 0.34 g, [M⁺+H]=560.97. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(1-phenylethyl)benzoic     acid amide; 0.26 g, [M⁺+H]=506.88. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2-phenylethyl     benzoic acid amide; 0.37 g, [M⁺+H]=507.01. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-[2-(4-phenoxy     phenyl)ethyl]benzoic acid amide; 0.36 g, [M⁺+H]=598.95. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(3-phenylpropyl)benzoic     acid amide; 0.31 g, [M⁺+H]=520.97. -   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(trans-2-phenylcyclopropyl)benzoic     acid amide; 0.21 g, [M⁺+H]=518.88.

Synthetic Example 2 Production of the Compound of the Present Invention by Use of L-COS Parallel Liquid-Phase Synthesis System of MORITEX Corporation

Ten (10) bials of L-COS in which stirrers were placed were assigned a number of 1 to 10, respectively. 1.0 mmol of 3-chloro-4-fluorophenyl boric acid was weighed in the bials of Nos. 1 and 6, 1.0 mmol of 3,5-bis(trifluoromethyl)phenyl boric acid was weighed in the bials of Nos. 2 and 7, 1.0 mmol of 3-trifluoromethylphenyl boric acid was weighed in the bials of Nos. 3 and 8, 1.0 mmol of 3-trifluoromethoxyphenyl boric acid was weighed in the bials of Nos. 4 and 9, and 1.0 mmol of 2-naphthyl boric acid was weighed in the bials of Nos. 5 and 10, Then, 0.05 mmol of dichlorobis(triphenylphosphine) palladium (II) was added in each bial, the bial was filled with nitrogen and covered, and placed in a reaction vessel of L-COS. With stirring at room temperature, in each bial, 3 ml of a solution of 2-bromo-3,3,3-trifluoropropene in 1,2-dimethoxyethane (0.5 mmol/ml), 1.5 ml of water, and then 1 ml of a solution of triethylamine in 1,2-dimethoxyethane (6.0 mmol/ml) were added in that order, and stirred at 75° C. for 3.5 hours. Then, the bials were cooled to 0° C., 1.5 ml of a solution of N-benzyl-4-(chlrohydroxyiminomethyl)benzoic acid amide in 1,2-dimethoxyethane (0.7 mmol/ml) was added in the bials of Nos. 1 to 5, and 1.5 ml of a solution of 4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 1,2-dimethoxyethan (0.7 mmol/ml) was added in the bials of Nos. 6 to 10, and the bials were continued to stir at room temperature for 16 hours. After the completion of the reaction, the organic phase was collected, aqueous phase was extracted with 5 ml of chloroform, the chloroform was added to the organic phase, and the solvent was distilled off under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product was obtained as white to yellow solid. In addition, the product was confirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysis condition: 254 nm, 80% CH₃CN-20% H₂O-0.1% HCOOH, ionization: positive electrospray).

-   N-benzyl-4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.28 g, [M⁺+H]=476.80. -   N-benzyl-4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.25 g, [M⁺+H]=560.76. -   N-benzyl-4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.26 g, [M⁺+H]=492.82. -   N-benzyl-4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.25 g, [M⁺+H]=508.80. -   N-benzyl-4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic     acid amide; 0.09 g, [M⁺+H]=474.86. -   4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic     acid amide; 0.29 g, [M⁺+H]=468.76. -   4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic     acid amide; 0.29 g, [M⁺+H]=552.72. -   4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic     acid amide; 0.18 g, [M⁺+H]=484.78. -   4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic     acid amide; 0.27 g, [M⁺+H]=500.76. -   4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic     acid amide; 0.14 g, [M⁺+H]=466.83.

Synthetic Example 3 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 3-060) Step 1: Production of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene

In a solution of 25.0 g of 3,5-dichlorophenyl boric acid in 200 ml of tetrahydrofuran and 100 ml of water, 27.5 g of 2-bromo-3,3,3-trifluoropropene, 38.0 g of potassium carbonate and 1.84 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 3 hours. After the completion of the reaction and cooling to room temperature, 500 ml of ice water was added, and extracted with ethyl acetate (500 ml×1). The organic phase was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane, and 25.7 g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.41 (t, J=2.0 Hz, 1H), 7.3-7.35 (m, 2H), 6.05 (q, J=3.2 Hz, 1H), 5.82 (q, J=3.2 Hz, 1H).

Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid methyl ester

In a solution of 2.70 g of 4-(hydroxyiminomethyl)benzoic acid methyl ester in 15 ml of N,N-dimethylformamide, 2.04 g of N-chlorosuccinic acid imide was added, and stirred at 40° C. for 40 minutes. Then, the reaction mixture was cooled to 0° C., 3.40 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene and 1.72 g of triethylamine were added, continued to stir at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured into 100 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to 1:3 gradient), and 4.05 g of the aimed product was obtained as white crystal.

Melting point 94.0 to 96.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.10 (d, J=8.4 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.43 (s, 2H), 7.26 (s, 1H), 4.12 (d, J=17.3 Hz, 1H), 3.94 (s, 3H), 3.74 (d, J=17.3 Hz, 1H).

Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid

In a solution of 3.99 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid methyl ester in 50 ml of methanol, a solution of 2.00 g of potassium hydroxide in 25 ml of water was added, stirred at room temperature for 3 days and then at 40° C. for 5 hours. After the completion of the reaction, the reaction mixture was cooled with ice, and poured in 200 ml of water, and adjusted to pH 1-2 with concentrated hydrochloric acid, and then extracted with ethyl acetate (50 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 3.87 g of the aimed product as pale yellow crystal.

Melting point 237.0 to 240.0° C.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 8.09 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.54 (s, 2H), 7.44 (s, 1H), 4.18 (d, J=17.7 Hz, 1H), 3.86 (d, J=17.7 Hz, 1H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoro ethyl)benzoic acid amide

In a suspension of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid in 10 ml of benzene, 0.44 g of thionyl chloride and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added, and stirred under reflux with heat for 2.5 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure to obtain 1.81 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid chloride as pale yellow oily substance.

In a solution of 0.29 g of 2,2,2-trifluoroethylamine and 0.37 g of triethylamine in 20 ml of chloroform, 1.81 g of the crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid chloride dissolved in 10 ml of chloroform was added dropwise with cooling with ice and with stirring. After the completion of addition dropwise, the mixture was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and extracted with chloroform (20 ml×3), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and passed through a glass filter packed with silica gel, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 1.05 g of the aimed product as white crystal.

Melting point 94.0 to 96.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.86 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.51 (s, 2H), 7.44 (s, 1H), 6.47 (t, J=6.3 Hz, 1H), 4.14 (qd, J=18.5, 6.3 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H).

Synthetic Example 4 N-Benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro benzoic acid amide (Compound of the present invention No. 5-039) Step 1: Production of 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.50 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole synthesized from 3-fluoro-4-methylphenylaldoxime and 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene similarly to Step 2 of Synthetic Example 3 in 50 ml of 1,2-dichloroethane, 0.68 g of N-bromosuccinic acid imide and a catalytic amount of azobisisobutyronitrile were added, and stirred under nitrogen atmosphere and under reflux with heat for 1 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, poured in 50 ml of water, extracted with chloroform (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.45-7.6 (m, 6H), 4.51 (s, 2H), 4.05 (d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H).

Step 2: Production of 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of crude 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 ml of acetic acid, 1.50 g of potassium acetate was added, and stirred under reflux with heat for 1.5 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and neutralized by pouring in 100 ml of saturated sodium hydrogen carbonate aqueous solution. The organic phase was collected, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.50 g of crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.2-7.55 (m, 6H), 5.20 (s, 2H), 4.05 (d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H), 2.14 (s, 3H).

Step 3: Production of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.50 g of crude 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 10 ml of ethanol, 2.00 g of sodium hydroxide dissolved in 20 ml of water was added, and stirred under reflux with heat for 4.5 hours. After the completion of the reaction, the reaction mixture was cooled with ice, and adjusted to pH 2-3 by carefully adding concentrated hydrochloric acid, and extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.95 g of the aimed product as pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.5-7.6 (m, 3H), 7.4-7.45 (m, 3H), 4.81 (s, 2H), 4.06 (d, J=17.2 Hz, 1H), 3.68 (d, J=17.2 Hz, 1H), 1.87 (bs, 1H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro benzoic acid

In a solution of 0.95 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 25 ml of acetone, Johnes' Reagent prepared from 1.50 g of chromic acid, 1.2 ml of concentrated sulfuric acid and 7 ml of water was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at room temperature for further 1.5 hour. After the completion of the reaction, the reaction mixture was poured in 50 ml of water and extracted with diethyl ether (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 0.67 g of the aimed product as beige crystal.

Melting point 172.0 to 174.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.05-8.15 (m, 1H), 7.45-7.55 (m, 5H), 4.08 (d, J=17.3 Hz, 1H), 3.71 (d, J=17.3 Hz, 1H).

Step 5: Production of N-benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro benzoic acid amide

In a solution of 0.15 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro benzoic acid in 10 ml of dichloromethane, 0.3 ml of oxalyl chloride and 2 drops of N,N-dimethylformamide were added at room temperature, and stirred at the same temperature for 10 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, the remaining white solid was dissolved in 10 ml of chloroform, and 0.3 ml of benzylamine and then 0.3 ml of triethylamine were added under cooling with ice, after the completion of the addition, continued to stir at room temperature for further 20 minutes. After the completion of the reaction, 40 ml of water was poured in the reaction mixture, and extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.14 g of the aimed product as white crystal.

Melting point 172.0 to 176.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.20 (t, J=8.0 Hz, 1H), 7.25-7.55 (m, 10H), 7.05 (t, J=5.6 Hz, 1H), 4.68 (d, J=5.6 Hz, 2H), 4.07 (d, J=17.6 Hz, 1H), 3.70 (d, J=17.6 Hz, 1H).

Synthetic Example 5 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-339) Step 1: Production of 4-bromo-3-nitrobenzaldoxime

In a solution of 5.0 g of 4-bromo-3-nitrobenzaldehyde in 50 ml of methanol,

3.6 ml of 50% hydroxyamine aqueous solution was added with stirring at room temperature, and continued to stir at the same temperature for 18 hours. After the completion of the reaction, 60 ml of water was added in the reaction mixture, and precipitated solid was filtered off, washed with water and then dried to obtain 5.0 g of the aimed product as yellow crystal.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 400 MHz) δ 11.18 (s, 1H), 8.09 (s, 1H), 8.07 (d, J=2.0 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.62 (dd, J=8.4, 2.0 Hz, 1H).

Step 2: Production of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.27 g of 4-bromo-3-nitrobenzaldoxime in 16 ml of N,N-dimethylformamide, 0.74 g of N-chlorosuccinic acid imide was added, and stirred at 35° C. for 90 minutes. Then, the reaction mixture was cooled with ice, 1.20 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.60 g of triethylamine were added, continued to stir at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to 1:4 gradient), and 1.10 g of the aimed product was obtained as yellow crystal.

Melting point 179.0 to 181.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.06 (d, J=2.0 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.78 (dd, J=8.4, 2.0 Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8 Hz, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H).

Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitrobenzoic acid ethyl ester

In a solution of 2.0 g of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 ml of ethanol in an autoclave, 0.40 g of sodium acetate, 88.0 mg of 1,1′-bis(diphenylphosphino) ferrocene and 18.0 mg of palladium (II) acetate were added, and stirred under 0.9 MPa carbon monoxide atmosphere at 100° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the solvent was distilled off under reduced pressure, and the residue was dissolved in 100 ml of ethyl acetate, washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to 1:4 gradient), and 0.66 g of the aimed product was obtained as pale yellow crystal.

Melting point 160.0 to 162.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.13 (d, J=1.6 Hz, 1H), 7.99 (dd, J=8.1, 1.6 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 4.11 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.8 Hz, 1H), 1.37 (t, J=7.1 Hz, 3H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 0.36 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitrobenzoic acid ethyl ester in 8 ml of ethanol, a solution of 0.40 g of potassium hydroxide in 2 ml of water was added, and stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was poured in 15 ml of water, adjusted to pH 4 with concentrated hydrochloric acid, then extracted with ethyl acetate (20 ml×2), the organic phase was washed with water, and then dehydrated with saturated sodium chloride aqueous solution and dried over over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 0.40 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitro benzoic acid as pale yellow oily substance. The substance was dissolved in 10 ml of chloroform, and 0.24 g of 2-picolylamine, 0.01 g of 4-(N,N-dimethylamino)pyridine and 0.35 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at room temperature for 18 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to 1:0 gradient), and 0.14 g of the aimed product was obtained as colorless resinous substance.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 8.50 (d, J=4.8 Hz, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.03 (dd, J=8.1, 1.6 Hz, 1H), 7.72 (td, J=7.7, 1.6 Hz, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.51 (d, J=1.5 Hz, 2H), 7.45 (t, J=1.8 Hz, 1H), 7.43 (bs, 1H), 7.36 (d, J=7.9 Hz, 1H), 7.23 (dd, J=6.8, 5.3 Hz, 1H), 4.76 (d, J=4.8 Hz, 2H), 4.13 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H).

Synthetic Example 6 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-317) Step 1: Production of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate

In a solution of 3.0 g of 4-hydroxy-3-methoxybenzaldehyde and 2.4 g of triethylamine in 50 ml of dichloromethane, 5.8 g of trifluoromethane sulfonic acid anhydride was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at the same temperature for 30 minutes. After the completion of the reaction, the reaction mixture was washed with 50 ml of water and then with 30 ml of saturated sodium hydrogen carbonate aqueous solution, and dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in a mixture of 30 ml of ethanol and 15 ml of water, 1.4 g of hydroxyamine hydrochloride and 1.7 g of sodium acetate were added with stirring at room temperature, and continued to stir at the same temperature for further 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, extracted with ethyl acetate (40 ml×2), the organic phase was washed with water (30 ml×1), and then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 5.25 g of the aimed product as brown oily substance.

Refractive index n_(D) ^(20.2° C.)=1.5082

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 8.47 (bs, 1H), 8.11 (s, 1H), 7.32 (s, 1H), 7.24 (d, J=8.1 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 3.94 (s, 3H).

Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxyphenyl trifluoromethane sulfonate

In a solution of 2.0 g of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate in 30 ml of N,N-dimethylformamide, 0.9 g of N-chlorosuccinic acid imide was added, and stirred at 40 to 50° C. for 30 minutes. Then, the reaction mixture was left and cooled to room temperature, 1.5 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.7 g of triethylamine were added, and stirred at room temperature for 90 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:7), and 1.4 g of the aimed product was obtained as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.50 (s, 2H), 7.44 (s, 1H), 7.25-7.3 (m, 2H), 7.11 (d, J=8.4 Hz, 1H), 4.08 (d, J=17.1 Hz, 1H), 3.97 (s, 3H), 3.69 (d, J=17.1 Hz, 1H).

Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy benzoic acid ethyl ester

In a solution of 1.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxyphenyl trifluoromethane sulfonate in 25 ml of ethanol in an autoclave, 0.27 g of sodium acetate, 31.0 mg of 1,1′-bis(diphenylphosphino) ferrocene and 7.0 mg of palladium (II) acetate were added, and stirred under 0.96 MPa carbon monoxide atmosphere at 100° C. for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (40 ml×2). The organic phases together were dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:5), and 1.20 g of the aimed product was obtained as white crystal.

Melting point 142.0-144.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.82 (d, J=7.8 Hz, 1H), 7.51 (s, 2H), 7.4-7.45 (m, 2H), 7.10 (d, J=7.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.95 (s, 3H), 3.71 (d, J=17.4 Hz, 1H), 1.39 (t, J=7.2 Hz, 3H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy benzoic acid

In a solution of 1.07 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy benzoic acid ethyl ester in 30 ml of ethanol, a solution of 1.0 g of sodium hydroxide in 30 ml of water was added, stirred at 85° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was adjusted to pH 2 to 3 with concentrated hydrochloric acid, and extracted with ethyl acetate (30 ml×2). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.0 g of the aimed product as pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 10.67 (bs, 1H), 8.24 (d, J=7.8 Hz, 1H), 7.57 (s, 1H), 7.51 (s, 2H), 7.45 (s, 1H), 7.22 (d, J=7.8 Hz, 1H), 4.05-4.15 (m, 4H), 3.74 (d, J=17.4 Hz, 1H).

Step 5: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a suspension of 0.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methoxy benzoic acid in 15 ml of dichloromethane, 0.09 g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added, and stirred at room temperature for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 15 ml of dichloromethane, and 0.09 g of triethylamine was added under cooling with ice, then 0.07 g of 2,2,2-trifluoroethylamine was added dropwise. After the completion of addition dropwise, the mixture was continued to stir at the same temperature for further 2 hours. Thereafter, the reaction mixture was diluted with 60 ml of chloroform, washed with 50 ml of water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.25 g of the aimed product as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.2-8.3 (m, 2H), 7.51 (s, 3H), 7.43 (s, 1H), 7.17 (d, J=7.8 Hz, 1H), 4.05-4.2 (m, 3H), 4.05 (s, 3H), 3.74 (d, J=17.4 Hz, 1H).

Synthetic Example 7 4-[5-(4-Fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 3-141) Step 1: Production of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a suspension of 1.00 g of 4-formyl benzoic acid in 15 ml of benzene, 0.87 g of thionyl chloride and 2 drops of N,N-dimethylformamide were added, and stirred under reflux with heat for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain 1.14 g of crude 4-formyl benzoic acid chloride as white crystal. In a solution of 0.66 g of 2,2,2-trifluoroethylamine and 0.81 g of triethylamine in 6 ml of chlororform, the solution of 1.14 g of the crude 4-formyl benzoic acid chloride in 6 ml of chloroform was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at room temperature for further 18 hours. After the completion of the reaction, the reaction mixture was added in 30 ml of water, extracted with chloroform (20 ml×3). The organic phase was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, the residual solid was washed with hexane to obtain 1.32 g of the aimed product as white crystal.

Melting point 83.0 to 84.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 10.09 (s, 1H), 7.96 (bs, 4H), 6.80 (bs, 1H), 4.05-4.25 (m, 2H).

Step 2: Production of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 4.11 g of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 30 ml of ethanol and 10 ml of water, 1.99 g of hydroxyamine hydrochloride and 2.51 g of anhydrous sodium acetate were added, stirred at room temperature for 3.5 hours. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and then extracted with ethyl acetate (30 ml×3), the organic phase was washed with 50 ml of saturated sodium hydrogen carbonate aqueous solution, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 3.92 g of the aimed product as white crystal.

Melting point 153.0 to 154.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 10.89 (s, 1H), 8.08 (s, 1H), 8.03 (bs, 1H), 7.84 (d, J=8.2 Hz, 2H), 7.60 (d, J=8.2 Hz, 2H), 3.95-4.1 (m, 2H).

Step 3: Production of 4-chlorohydroxyiminomethyl-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 3.80 g of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 50 ml of tetrahydrofyran, 20 ml of 3N hydrochloric acid was added, 14 ml of 8% sodium hypochlorite aqueous solution was added dropwise with stirring under ice cooling over 10 minutes, after the completion of addition dropwise, continued to stir at the same temperature for further 15 minutes. After the completion of the reaction, the reaction mixture was poured in 200 ml of water, extracted with ethyl acetate (30 ml×3), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 4.15 g of the product as white crystal.

Melting point 158.0 to 160.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 12.03 (s, 1H), 8.05 (t, J=6.0 Hz, 1H), 7.93 (bs, 4H), 3.95-4.15 (m, 2H).

Step 4: Production of 4-[5-(4-fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydrooxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.21 g of 4-fluoro-3-methylphenyl boric acid and 0.23 g of 2-bromo-3,3,3-trifluoropropene in 6 ml of 1,2-dimethoxyethane and 2 ml of water, 0.24 g of sodium carbonate and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, stirred at 75° C. for 3 hours. Then, the reaction mixture was left and cooled to room temperature, then a solution of 0.25 g of 4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 4 ml of 1,2-dimethoxyethane was added, continued to stir at the same temperature for further 18 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of water, extracted with ethyl acetate (10 ml×3), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual solid was purified with silica gel column chromatography that was eluated with chloroform to obtain 0.24 g of the product as white crystal.

Melting point 151.0 to 152.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.86 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.35-7.5 (m, 2H), 7.0-7.15 (m, 1H), 6.39 (t, J=6.3 Hz, 1H), 4.05-4.25 (m, 2H), 4.09 (d, J=17.3 Hz, 1H), 3.74 (d, J=17.3 Hz, 1H), 2.32 (d, J=1.7 Hz, 3H).

Synthetic Example 8 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-075) Step 1: Production of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 5.00 g of 4-bromo-2-methyl benzoic acid and 3.45 g of 2,2,2-trifluoroethylamine in 30 ml of N,N-dimethylformamide, 5.79 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added with stirring at room temperature, and stirred at the same temperature for 1.5 hour. After the completion of the reaction, 80 ml of water was added, and precipitated crystal was filtered off, washed with water and dried to obtain 4.00 g of the aimed product as white crystal.

Melting point 124.0 to 125.5° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.40 (s, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.15 (bs, 1H), 4.0-4.15 (m, 2H), 2.39 (s, 3H).

Step 2: Production of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 1.00 g of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 15 ml of tetrahydrofuran under nitrogen atmosphere, 4.7 ml of n-butyl lithium (1.58M hexane solution) was added dropwise at −70° C. with stirring, and then 0.4 ml of N,N-dimethylformamide were added dropwise. After stirring at the same temperature for 30 minutes, 10 ml of 1N hydrochloric acid and then 30 ml of water were added, and extracted with ethyl acetate (30 ml×2). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 0.80 g of the aimed product as pale yellow crystal.

Melting point 99.0 to 104.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 10.00 (s, 1H), 7.7-7.75 (m, 2H), 7.50 (d, J=7.5 Hz, 1H), 6.27 (bs, 1H), 4.05-4.2 (m, 2H), 2.49 (s, 3H).

Step 3: Production of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.8 g of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 10 ml of ethanol and 5 ml of water, 0.3 g of hydroxyamine hydrochloride and 0.4 g of anhydrous sodium acetate were added with stirring at room temperature, and stirred at the same temperature for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, and precipitated crystal was filtered off, washed with water and dried to obtain 0.5 g of the aimed product as white crystal.

Melting point 190.5 to 194.0° C.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 400 MHz) δ 10.98 (s, 1H), 8.43 (bs, 1H), 8.07 (s, 1H), 7.35-7.55 (m, 3H), 3.95-4.1 (m, 2H), 2.43 (s, 3H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.40 g of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 15 ml of N,N-dimethylformamide, 0.21 g of N-chlorosuccinc acid imide was added, and stirred at 50° C. for 30 minutes. Then, the reaction mixture was left and cooled to room temperature, 0.34 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.16 g of triethylamine were added, and stirred at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.45 g of the aimed product was obtained as white crystal.

Melting point 155.5 to 157.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.4-7.55 (m, 6H), 6.13 (bs, 1H), 4.05-4.2 (m, 3H), 3.71 (d, J=17.4 Hz, 1H), 2.45 (s, 3H).

Synthetic Example 9 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-234) Step 1: Production of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 3.0 g of 4-bromo-2-methyl benzoic acid in 30 ml of dichloromethane, 2.7 g of oxalyl chloride and 3 drops of N,N-dimethylformamide were added under cooling with ice with stirring, and stirred at room temperature for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 30 ml of dichloromethane, 2.1 g of triethylamine and 2.0 g of 2-picolylamine were added under cooling with ice with stirring, and continued to stir at room temperature for 3 hours. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with chloroform (50 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with diisopropylether to obtain 3.7 g of the aimed product as yellow crystal.

Melting point 86.0 to 87.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.52 (d, J=4.8 Hz, 1H), 7.69 (td, J=7.8, 1.8 Hz, 1H), 7.15-7.4 (m, 6H), 4.73 (d, J=4.8 Hz, 2H), 2.45 (s, 3H).

Step 2: Production of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 2.0 g of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 20 ml of N,N-dimethylformamide in an autoclave, 0.67 g of sodium formate and 0.10 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under 1.05 MPa carbon monoxide atmosphere at 110° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and poured in 100 ml of water, and extracted with ethyl acetate (50 ml×2). The organic phases together were dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (9:1), and 0.50 g of the aimed product was obtained as pale yellow crystal.

Melting point 79.5 to 83.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 10.02 (s, 1H), 8.54 (d, J=5.1 Hz, 1H), 7.6-7.8 (m, 4H), 7.15-7.4 (m, 3H), 4.77 (d, J=4.8 Hz, 2H), 2.55 (s, 3H).

Step 3: Production of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 0.50 g of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 10 ml of ethanol and 5 ml of water, 0.18 g of hydroxyamine hydrochloride was added with stirring at room temperature, and stirred at the same temperature for 12 hours. After the completion of the reaction, solid was filtered off, ethanol was distilled off under reduced pressure, and 30 ml of saturated sodium hydrogen carbonate aqueous solution was added in the remaining aqueous solution. The precipitated crystal was filtered off, washed with water and dried to obtain 0.45 g of the aimed product as pale yellow crystal.

Melting point 159.5 to 161.0° C.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 11.89 (bs, 1H), 8.56 (d, J=4.2 Hz, 1H), 8.03 (s, 1H), 7.90 (bs, 1H), 7.77 (t, J=7.8 Hz, 1H), 7.47 (d, J=7.5 Hz, 1H), 7.0-7.35 (m, 4H), 4.76 (d, J=6.0 Hz, 2H), 2.36 (s, 3H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 0.45 g of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 10 ml of N,N-dimethylformamide, 0.25 g of N-chlorosuccinc acid imide was added, and stirred at 70° C. for 1 hour. Then, the reaction mixture was left and cooled to room temperature, 0.41 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.25 g of potassium hydrogen carbonate were added, and stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (60 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1), and 0.30 g of the aimed product was obtained as white crystal.

Melting point 131.0 to 135.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.53 (d, J=5.0 Hz, 1H), 7.65-7.75 (m, 1H), 7.2-7.55 (m, 9H), 4.75 (d, J=4.9 Hz, 2H), 4.09 (d, J=17.3 Hz, 1H), 3.71 (d, J=17.3 Hz, 1H), 2.50 (s, 3H).

Synthetic Example 10 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide (Compound of the present invention No. 5-315) Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-iodo benzoic acid methyl ester

In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-iodo benzoic acid synthesized similarly to Steps 1 to 4 of Synthetic Example 4 in 10 ml of methanol, 2 drops of concentrated sulfuric acid was added, and stirred under reflux with heat for 20 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was neutralized with 10 ml of saturated sodium hydrogen carbonate aqueous solution, then extracted with ethyl acetate (10 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.56 g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.22 (d, J=1.5 Hz, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.75-7.8 (m, 1H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.07 (d, J=17.7 Hz, 1H), 3.95 (s, 3H), 3.69 (d, J=17.2 Hz, 1H).

Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-trifluoromethyl benzoic acid methyl ester

In a solution of 0.51 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-iodo benzoic acid methyl ester in 5 ml of N,N-dimethylformamide, 0.18 g of copper (I) iodide, 0.06 g of potassium fluoride and 0.27 g of chlorodifluoro acetic acid methyl ester were added, and stirred at 120° C. for 5 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 50 ml of water was added and extracted with ethyl acetate (50 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.45 g of the aimed product was obtained as pale yellow oily substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.00 (d, J=1.1 Hz, 1H), 7.85-7.95 (m, 2H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.12 (d, J=7.1 Hz, 1H), 3.96 (s, 3H), 3.94 (d, J=7.8 Hz, 1H).

Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-trifluoromethyl benzoic acid

In a solution of 0.40 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-trifluoromethyl benzoic acid methyl ester in 5 ml of methanol, a solution of 0.10 g of sodium hydroxide in 2 ml of water was added, and stirred at room temperature for 18 hours. After the completion of the reaction, 10 ml of water was added in the reaction mixture, washed with 5 ml of toluene, aqueous phase was collected, adjusted to pH 1 to 2 with concentrated hydrochloric acid and then extracted with ethyl acetate (20 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.34 g of the aimed product as pale yellow resinous substance. The resulting product was used as such without purification for the next step.

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide

In a solution of 0.15 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-trifluoromethyl benzoic acid in 3 ml of dichloromethane, 0.06 g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added under cooling with ice with stirring, and stirred at room temperature for 2 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 3 ml of dichloromethane, and a solution of 0.05 g of 2-picolylamine and 0.06 g of triethylamine in 1 ml of dichloromethane was added dropwise, after the completion of the addition dropwise, continued to stir at room temperature for 3 hours. After the completion of the reaction, 5 ml of water was added in the reaction mixture, extracted with chloroform (5 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:3), and 0.05 g of the aimed product was obtained as white crystal.

Melting point 69.0 to 70.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.5-8.55 (m, 1H), 7.95 (bs, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m, 2H), 7.35-7.45 (m, 3H), 7.26 (t, J=4.9 Hz, 1H), 4.77 (d, J=4.9 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.2 Hz, 1H).

Synthetic Example 11 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-344) Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-phenyl benzoic acid methyl ester

In a solution of 0.70 g of 2-bromo-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid methyl ester synthesized similarly to Step 1 of Synthetic Example 10 in 20 ml of tetrahydrofuran and 10 ml of water, 0.18 g of phenyl boric acid, 0.39 g of potassium carbonate and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 1.5 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was poured in 30 ml of water, then extracted with ethyl acetate (50 ml×1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate, and 0.78 g of the aimed product was obtained as brown resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.89 (d, J=8.4 Hz, 1H), 7.74 (dd, J=8.0, 1.8 Hz, 1H), 7.62 (d, J=1.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 2H), 7.35-7.45 (m, 4H), 7.25-7.35 (m, 2H), 4.11 (d, J=16.8 Hz, 1H), 3.73 (d, J=16.8 Hz, 1H), 3.65 (s, 3H).

Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-phenyl benzoic acid

In a solution of 0.78 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-phenyl benzoic acid methyl ester in 15 ml of ethanol, a solution of 0.30 g of sodium hydroxide in 15 ml of water was added, and stirred at 60° C. for 3 hours. After the completion of the reaction, ethanol was distilled off under reduced pressure, adjusted to pH 1 to 2 with 12N hydrochloric acid, and then extracted with ethyl acetate (50 ml×1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.70 g of the aimed product as brown glass substance. The resulting product was used as such without purification for the next step.

Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 0.3 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-phenyl benzoic acid in 10 ml of chloroform, 0.3 ml of oxalyl chloride and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added with stirring at room temperature, and stirred at the same temperature for 10 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 10 ml of chloroform, and under cooling with ice with stirring 0.3 ml of 2-picolylamine and then 0.3 ml of triethylamine were added, and continued to stir at room temperature for 20 minutes. After the completion of the reaction, the reaction mixture was poured in 40 ml of water, extracted with ethyl acetate (50 ml×1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:1), and 0.2 g of the aimed product was obtained as white crystal.

Melting point 194.0 to 198.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.3-8.35 (m, 1H), 7.25-7.8 (m, 12H), 7.1-7.15 (m, 1H), 7.40 (d, J=7.8 Hz, 1H), 6.65-6.7 (m, 1H), 4.47 (d, J=5.0 Hz, 2H), 4.12 (d, J=17.0 Hz, 1H), 3.74 (d, J=17.0 Hz, 1H).

Synthetic Example 12 2-Amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-329) Step 1: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid ethyl ester

In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitro benzoic acid ethyl ester synthesized in Steps 1 to 3 of Synthetic Example 5 in 6 ml of ethyl acetate, 2.0 ml of water, 0.6 ml of acetic acid and 0.46 g of reduced iron were added, and stirred at 75° C. for 2 hours. After the completion of the reaction, the organic phase was collected, and the aqueous phase was extracted with ethyl acetate (10 ml×2). The organic phases together were washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.60 g of crude aimed product as brown oily substance. The resulting product was used as such without purification for the next step.

Step 2: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid

In a solution of 0.6 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid ethyl ester in 7 ml of ethanol, a solution of 0.5 g of potassium hydroxide in 2.0 ml of water was added, and stirred at room temperature for 18 hours. After the completion of the reaction, 20 ml of ice water was added in the reaction mixture, adjusted to pH 2 to 3 with concentrated hydrochloric acid, and then extracted with ethyl acetate (20 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.6 g of crude aimed product as yellow oily substance. The resulting product was used as such without purification for the next step.

Step 3: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.60 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid in 6 ml of chloroform, 0.20 g of 2,2,2-trifluoroethylamine, 0.02 g of 4-(N,N-dimethylamino) pyridine and 0.33 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:4), and 0.14 g of the aimed product was obtained as pale yellow crystal.

Melting point 78.0 to 79.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.50 (d, J=1.8 Hz, 2H), 7.43 (t, J=1.8 Hz, 1H), 7.39 (d, J=8.6 Hz, 1H), 6.95-7.0 (m, 2H), 6.29 (t, J=7.0 Hz, 1H), 5.68 (bs, 2H), 4.05-4.15 (m, 2H), 4.04 (d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H).

Synthetic Example 13 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylthio-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-323)

In a solution of 0.92 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-041) synthesized similarly to Synthetic Example 4 in 12 ml of dimethylsulfoxide, 0.12 g of sodium methane thiolate was added with stirring at room temperature, and stirred at 100° C. for 90 minutes. After the completion of the reaction, the reaction mixture was poured in 30 ml of water, and extracted with ethyl acetate (20 ml×3). The organic phase was washed with 30 ml of water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with chloroform, and 0.89 g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.51 (d, J=4.8 Hz, 1H), 7.6-7.75 (m, 4H), 7.52 (bs, 2H), 7.42 (bs, 1H), 7.37 (bs, 1H), 7.34 (bs, 1H), 7.20 (dd, J=6.9, 1.8 Hz, 1H), 4.74 (d, J=4.8 Hz, 2H), 4.10 (d, J=17.1 Hz, 1H), 3.75 (d, J=17.1 Hz, 1H), 2.47 (s, 3H).

Synthetic Example 14 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylsulfinyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-324)

In a solution of 0.38 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-322) synthesized similarly to Synthetic Example 13 in 6 ml of 1,2-dichloroethane, 0.10 g of N-chlorosuccinic acid imide was added with stirring at room temperature, and stirred at the same temperature for 11 hours. After the completion of the reaction, the reaction mixture was poured in 30 ml of water, and extracted with ethyl acetate (20 ml×3). The organic phase was washed with 30 ml of saturated sodium hydrogen carbonate, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.17 g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.16 (t, J=8.1 Hz, 1H), 7.6-7.8 (m, 3H), 7.55 (d, J=8.1 Hz, 1H), 7.51 (d, J=8.1 Hz, 1H), 7.15 and 7.11 (t, J=6.3 Hz, 1H), 4.18 (qd, J=18.5, 6.3 Hz, 2H), 4.15 (d, J=17.7 Hz, 1H), 3.80 (d, J=17.7 Hz, 1H), 2.79 and 2.78 (s, 3H).

Synthetic Example 15 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylsulfonyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-326)

In a solution of 0.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-322) synthesized similarly to Synthetic Example 13 in 6 ml of dichloromethane, 0.17 g of 3-chloroperbenzoic acid was added with stirring at room temperature, and stirred at the same temperature for 3 days. After the completion of the reaction, the reaction mixture was poured in 30 ml of sodium thiosulfate aqueous solution, and extracted with chloroform (10 ml×3). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with chloroform, and 0.20 g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.16 (t, J=8.4 Hz, 1H), 8.05 (bs, 1H), 8.00 (s, 1H), 7.92 (s, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.06 and 7.02 (t, J=6.4 Hz, 1H), 4.17 (d, J=17.4 Hz, 1H), 4.16 (qd, J=18.5, 6.3 Hz, 2H), 3.79 (d, J=17.4 Hz, 1H), 2.12 (s, 3H).

Synthetic Example 16 2-Cyano-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-341)

In a solution of 0.19 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-iodo-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-065) synthesized similarly to Synthetic Example 4 in 10 ml of dimethylacetamide, 36.0 mg of zinc cyanide, 4.8 mg of zinc, 11.0 mg of tris(dibenzylideneacetone) dipalladium and 13.5 mg of 1,1′-bis(diphenylphosphino)ferrocene were added, and stirred under nitrogen atmosphere at 80 to 120° C. for 5 hours. After the completion of the reaction, 30 ml of ammonia water and 20 ml of water were added in the reaction mixture, and extracted with ethyl acetate (50 ml×1). The organic phase was washed with 30 ml of water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethylacetate-hexane (2:1), and 0.05 g of the aimed product was obtained as brown resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.5-8.6 (m, 1H), 8.12 (bs, 1H), 7.9-8.0 (m, 2H), 7.15-7.7 (m, 7H), 5.13 (bs, 2H), 4.14 (d, J=17.4 Hz, 1H), 3.78 (d, J=17.4 Hz, 1H).

Synthetic Example 17 2-Acetylamino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-333)

In a solution of 0.05 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-329) synthesized in Synthetic Example 12 and 0.15 ml of triethylamine in 2 ml of chloroform, 0.10 ml of acetic anhydride was added under cooling with ice with stirring, and stirred at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:8 to 1:1 gradient), and 0.045 g of the aimed product was obtained as pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 10.90 (bs, 1H), 8.77 (d, J=1.3 Hz, 1H), 7.57 (dd, J=8.4, 1.5 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.50 (d, J=1.7 Hz, 2H), 7.45 (t, J=1.8 Hz, 1H), 6.82 (bs, 1H), 4.1-4.2 (m, 2H), 4.11 (d, J=17.0 Hz, 1H), 3.73 (d, J=17.0 Hz, 1H), 2.22 (s, 3H).

Synthetic Example 18 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-331) and 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-334)

In a solution of 0.25 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-329) synthesized in Synthetic Example 12 and 0.06 g of 36% formaldehyde aqueous solution in 7 ml of 1,2-dichloroethane, 1.00 g of sodium triacetoxy borohydride was added with stirring at room temperature in three portions at 1 hour-interval, and continued to stir at the same temperature for further 2 hours. After the completion of the reaction, the reaction mixture was poured to 5 ml of ice water, the organic phase was collected, and the solvent was distilled under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (0:1 to 1:3 gradient), and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide was obtained as pale yellow crystal, and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide was obtained as pale yellow resinous substance. 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide;

Melting point 156.0 to 158.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.57 (bs, 1H), 7.52 (d, J=1.6 Hz, 2H), 7.43 (t, J=1.8 Hz, 1H), 7.38 (d, J=8.2 Hz, 1H), 6.92 (d, J=1.6 Hz, 1H), 6.84 (dd, J=8.2, 1.6 Hz, 1H), 6.31 (t, J=6.4 Hz, 1H), 4.0-4.15 (m, 2H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.91 (s, 3H).

4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide;

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 10.29 (t, J=6.2 Hz, 1H), 8.22 (d, J=8.1 Hz, 1H), 7.73 (d, J=1.7 Hz, 1H), 7.52 (d, J=1.7 Hz, 2H), 7.44 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.1, 1.6 Hz, 1H), 4.13 (qd, J=9.2, 6.2 Hz, 2H), 4.10 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.78 (s, 6H).

Synthetic Example 19 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2-methoxyiminoethyl)-2-methyl benzoic acid amide (Compound of the present invention No. 5-113)

In a solution of 152 mg of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(2,2-dimethoxyethyl)-2-methyl benzoic acid amide (Compound of the present invention No. 5-083) synthesized similarly to Synthetic Example 5 in 14 ml of methanol-water (6:1) mixed solvent, 38 mg of methoxyamine hydrochloride was added, and stirred under reflux with heat for 8 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, diluted by adding 80 ml of ethyl acetate, washed with water (30 ml×2), and dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethylacetate-hexane (1:1), and 102 mg of the aimed product was obtained as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.45-7.55 (m, 6H), 7.45-7.55 and 6.83 (t, J=4.5 Hz, 1H), 7.4-7.45 (m, 1H), 6.28 and 6.16 (t, J=4.7 Hz, 1H), 4.27 and 4.22 (t, J=4.7 Hz, 2H), 4.08 (d, J=17.1 Hz, 1H), 3.92 and 3.85 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.50 and 2.48 (s, 3H).

Synthetic Example 20 N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]glycine (Compound of the present invention No. 5-127)

In a solution of 2.6 g of methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]glycine (Compound of the present invention No. 5-128) synthesized similarly to Synthetic Example 5 in 10 ml of methanol, a solution of 1.0 g of potassium hydroxide in 10 ml of water was added with stirring at room temperature, and stirred at the same temperature for further 1 hour. After the completion of the reaction, 10 ml of 12N hydrochloric acid was added and extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.4 g of the aimed product as pale yellow resinous resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.55 (m, 6H), 6.35-6.85 (m, 2H), 4.23 (d, J=5.7 Hz, 2H), 4.08 (d, J=17.1 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H), 2.44 (s, 3H).

Synthetic Example 21 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N—[N-(2,2,2-trifluoroethyl) carbamoylmethyl]benzoic acid amide (Compound of the present invention No. 5-151)

In a solution of 1.00 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]glycine (Compound of the present invention No. 5-127) synthesized in Synthetic Example 20 in 30 ml of dichloromethane, 0.65 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added, and stirred at room temperature for 15 minutes, then 0.40 g of 2,2,2-trifluoroethylamine and 0.40 g of 4-(N,N-dimethylamino)pyridine were added and stirred at the same temperature for further 2 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:3), and then crystallized from hexane to obtain 0.48 g of the aimed product as white crystal.

Melting point 173.5 to 175.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.35-7.55 (m, 7H), 7.03 (t, J=5.1 Hz, 1H), 4.21 (d, J=5.1 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.85-4.0 (m, 2H), 3.71 (d, J=17.4 Hz, 1H), 2.43 (s, 3H).

Synthetic Example 22 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N—(N-phenylcarbamoylmethyl)benzoic acid amide (Compound of the present invention No. 5-169)

In a solution of 0.40 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]glycine (Compound of the present invention No. 5-127) synthesized in Synthetic Example 20 and 0.08 g of pyridine in 10 ml of dichloromethane, 0.12 g of pivaloyl chloride was added, and stirred at room temperature for 2 hours, then 0.50 g of aniline and 3 ml of triethylamine were added and stirred at the same temperature for further 1 hour. After the completion of the reaction, 20 ml of water was added in the reaction mixture and extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:1) to obtain 0.12 g of the aimed product as white crystal.

Melting point 181.0 to 183.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.54 (bs, 1H), 7.5-7.55 (m, 7H), 7.44 (t, J=2.0 Hz, 1H), 7.31 (t, J=8.0 Hz, 2H), 7.1-7.2 (m, 1H), 6.95 (bs, 1H), 4.34 (d, J=5.0 Hz, 2H), 4.19 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.49 (s, 3H).

Synthetic Example 23 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 6-020)

In a solution of 0.35 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-234) synthesized similarly to Synthetic Example 5 in 20 ml of N,N-dimethylformamide, 0.04 g of 55% oily sodium hydride was added under cooling with ice with stirring, and stirred at the same temperature for 30 minutes. Then, 0.12 g of methyl iodide was added and thereafter the temperature was raised to room temperature, and continued to stir at the same temperature for further 2 hours. After the completion of the reaction, the reaction mixture was diluted with 80 ml of ethyl acetate, washed with water (50 ml×2), dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with high performance liquid chromatography that was eluated with acetonitrile-water (85:15) to obtain 0.25 g of the aimed product as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.5-8.6 (m, 1H), 7.6-7.75 (m, 1H), 7.05-7.55 (m, 8H), 4.43 and 4.89 (bs, 2H), 4.06 and 4.09 (d, J=17.4 and 17.1 Hz, 1H), 3.68 and 3.71 (d, J=17.4 and 17.1 Hz, 1H), 2.85 and 3.13 (s, 3H), 2.35 and 2.38 (s, 3H).

Synthetic Example 24 7-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-1-methyl-3-(2-pyridylmethyl)-1,2,3,4-tetrahydroquinazoline-4-one (Compound of the present invention No. 6-071)

In a solution of 0.06 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylamino-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-332) synthesized similarly to Synthetic Example 18 in 5 ml of dichloromethane, 0.03 g of chloromethylether was added, and stirred at the same temperature for 15 hours After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1) to obtain 0.04 g of the aimed product as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.5-8.6 (m, 1H), 8.04 (d, J=7.8 Hz, 1H), 7.6-7.75 (m, 1H), 7.4-7.55 (m, 4H), 7.15-7.3 (m, 1H), 7.10 (bs, 1H), 6.95-7.05 (m, 1H), 4.86 (s, 2H), 4.06 (s, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.90 (s, 3H).

Synthetic Example 25 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid thioamide (Compound of the present invention No. 7-007)

A solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-075) synthesized in Synthetic Example 8 and 0.41 g of Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfide) in 15 ml of toluene was stirred under reflux with heat for 20 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the reaction mixture was diluted with 60 ml of ethyl acetate, washed with water (50 ml×1), then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1) to obtain 0.40 g of the aimed product as yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.2-7.5 (m, 7H), 4.55-4.7 (m, 2H), 4.06 (d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.38 (s, 3H).

Synthetic Example 26 4-[5-(3-Bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-014) Step 1: Production of 3-bromodifluoromethoxy-1-iodobenzene

In a suspension of 0.87 g of 55% oily sodium hydride in 20 ml of N,N-dimethylformamide, a solution of 4.00 g of 3-iodophenol in 10 ml of N,N-dimethylformamide was added dropwise with stirring under ice cooling, after the completion of the addition dropwise, stirred at room temperature for 30 minutes. The reaction mixture was added dropwise in a solution of 11.40 g of dibromodifluoromethane in 20 ml of N,N-dimethylformamide under cooling with ice with stirring, after the completion of the addition dropwise, continued to stir at room temperature for 2 hours. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with ethyl acetate (100 ml×1), the organic phase was washed with water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 2.10 g of the aimed product as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.65-7.7 (m, 1H), 7.55-7.65 (m, 1H), 7.2-7.3 (m, 1H), 7.15 (t, J=9.0 Hz, 1H).

Step 2: Production of 3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)benzene

In 10 ml of a solution of 1-trifluoromethylethenyl zinc bromide prepared according to the method described in documents in 1M tetrahydrofuran, 1.0 g of 3-bromodifluoromethoxy-1-iodobenzene and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 2 hours. After the completion of the reaction, the reaction mixture was poured in 20 ml of diluted hydrochloric acid, extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in hexane, and high polar impurities were excluded by treating with silica gel to obtain 0.77 g of crude aimed product as colorless oily substance. The resulting product was used as such without purification for the next step.

Step 3: Production of 4-[5-(3-bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.3 g of 4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide synthesized similarly to Steps 1 to 3 of Synthetic Example 7 and 0.2 g of crude 3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)benzene in 10 ml of 1,2-dimethoxyethane, 0.4 g of potassium hydrogen carbonate was added, and stirred at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured in 20 ml of water, extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.29 g of the aimed product as colorless glass substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.5-7.6 (m, 5H), 7.41 (d, J=7.8 Hz, 1H), 7.3-7.5 (m, 1H), 6.16 (t, J=6.6 Hz, 1H), 4.05-4.15 (m, 3H), 3.74 (d, J=17.2 Hz, 1H), 2.45 (s, 3H).

Synthetic Example 27 4-[5-Chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-355) Step 1: Production of 2,3′,5′-trichloro-2,2-difluoroacetophenone

In a solution of 5.0 g of 3,5-dichloro-1-iodobenzene in 50 ml of t-butylmethylether, 12.2 ml of n-butyl lithium (1.58M hexane solution) was added dropwise at −78° C. with stirring, after the completion of the addition dropwise, stirred at the same temperature for 30 minutes. 6.6 g of chlorodifluoroacetic acid methyl ester was added dropwise at −78° C. with stirring in the reaction mixture, after the completion of the addition dropwise, continued to stir at 0° C. for further 30 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of saturated ammonium chloride aqueous solution, extracted with ethyl acetate (100 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 4.6 g of crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.97 (s, 2H), 7.68 (s, 1H).

Step 2: Production of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]benzene

In a solution of 2.89 g of methyltriphenylphosphonium bromide in 15 ml of tetrahydrofuran, 0.91 g of potassium t-butoxide was added, and stirred at room temperature for 1 hour. Then, a solution of 2.00 g of 2,3′,5′-trichloro-2,2-difluoroacetophenone in 5 ml of tetrahydrofuran was added dropwise in the reaction mixture under cooling with ice with stirring, after the completion of the addition dropwise, continued to stir at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 1.50 g of the aimed product as yellow oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.40 (s, 1H), 7.35 (s, 2H), 5.99 (s, 1H), 5.65 (s, 1H).

Step 3: Production of 4-[5-chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.25 g of 4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide synthesized similarly to Steps 1 to 3 of Synthetic Example 7 and 0.26 g of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]benzene in 3 ml of 1,2-dimethoxyethane, 0.43 g of potassium hydrogen carbonate and a small amount of water were added, and stirred at room temperature for 15 hours. After the completion of the reaction, the reaction mixture was filtered and thereby solid substance was excluded, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 0.28 g of the aimed product as yellow oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.35-7.65 (m, 6H), 6.06 (t, J=6.1 Hz, 1H), 4.0-4.25 (m, 3H), 3.72 (d, J=17.1 Hz, 1H), 2.47 (s, 3H).

Synthetic Example 28 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 6-043) Step 1: Production of 5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.31 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 1.17 g of α-chloro-3-methyl-4-nitrobenzaldoxime in 10 ml of tetrahydrofuran, 1.15 g of potassium hydrogen carbonate and 1.50 g of water were added, and stirred at room temperature for 18 hours. After the completion of the reaction, tetrahydrofuran was removed from the reaction mixture, 3 ml of water was added, and stirred under colloing with ice for further 30 minutes. Precipitated crystal was filtered off, washed with 5 ml of water and then 5 ml of diisopropyl ether to obtain 1.29 g of the aimed product as white crystal.

Melting point 135.0 to 136.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.03 (d, J=7.5 Hz, 1H), 7.6-7.75 (m, 2H), 7.51 (bs, 2H), 7.44 (t, J=1.8 Hz, 1H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.64 (s, 3H).

Step 2: Production of 3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.23 g of 5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 10 ml of ethyl acetate, 5.0 ml of water, 5.0 ml of acetic acid and 0.66 g of reduced iron were added and stirred at 100° C. for 2 hours. After the completion of the reaction, the reaction mixture was filtered through Celite, 20 ml of water was added in the filtrate, extracted with ethyl acetate (20 ml×2). The organic phases together were washed with 10 ml of saturated sodium hydrogen carbonate aqueous solution, and then with 10 ml of water, thereafter dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.05 g of crude aimed product as red-brown oily substance. The resulting product was used as such without purification for the next step.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.52 (s, 2H), 7.35-7.5 (m, 2H), 7.31 (dd, J=8.0, 2.0 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 4.05 (d, J=17.1 Hz, 1H), 3.93 (bs, 2H), 3.64 (d, J=17.1 Hz, 1H), 2.17 (s, 3H).

Step 3: Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 0.50 g of 3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 1.0 ml of 1,4-dioxane and 2.0 ml of water, 1.0 ml of 47% hydrobromic acid was added, and stirred under reflux with heat for 1 hour. Then, the reaction mixture was cooled with ice, and a solution of 0.10 g of sodium nitrite in 1.0 ml of water was slowly added dropwise with stirring at a temperature of 5° C. or less, after the completion of the addition dropwise, continued to stir at the same temperature for further 1 hour. The diazo mixture was slowly added dropwise in a mixture of 1.0 ml of 47% hydrobromic acid and 0.28 g of copper (I) bromide at 60° C. with stirring, after the completion of the addition dropwise, continued to stir at 60° C. for further 2 hours. After the completion of the reaction, 10 ml of water was added in the reaction mixture, extracted with ethyl acetate (20 ml×2), the organic phases together were washed with water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:10) to obtain 0.43 g of the aimed product as pale yellow crystal.

Melting point 105.0 to 108.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.59 (d, J=8.4 Hz, 1H), 7.45-7.55 (m, 3H), 7.42 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.4, 2.1 Hz, 1H), 4.07 (d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.43 (s, 3H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid ethyl ester

In a solution of 15.0 g of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 60 ml of ethanol in an autoclave, 3.26 g of sodium acetate, 0.37 g of 1,1′-bis(diphenylphosphino) ferrocene and 0.08 g of palladium (II) acetate were added, and stirred under 2.0 MPa carbon monoxide atmosphere at 110° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 200 ml of water was added and extracted with ethyl acetate (200 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:8) to obtain 10.8 g of the aimed product as colorless clear liquid. Refractive index n_(D) ^(21.4° C.)=1.5474

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.95 (d, J=8.4 Hz, 1H), 7.45-7.65 (m, 4H), 7.43 (t, J=1.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J=7.2 Hz, 3H).

Step 5: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid

In a solution of 10.79 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid ethyl ester in 50 ml of ethanol and 10 ml of water, a solution of 2.0 g of sodium hydroxide in 10 ml of water was slowly added with stirring at room temperature. Then, the reaction mixture was stirred at 80° C. for 2 hours, after the completion of the reaction, ethanol was distilled off under reduced pressure. The residue was adjusted to pH 1-2 with concentrated hydrochloric acid with stirring at 50° C., then continued to stir at the same temperature for 1 hour and then at 5° C. for 1 hour. Precipitated crystal was filtered off, washed with water and dried to obtain 9.36 g of the aimed product as white crystal.

Melting point 146.0 to 148.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.12 (d, J=8.7 Hz, 1H), 7.5-7.7 (m, 2H), 7.52 (d, J=1.5 Hz, 2H), 7.43 (d, J=1.5 Hz, 1H), 4.11 (d, J=16.8 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.69 (s, 3H).

Step 6: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid in 30 ml of toluene, 0.43 g of thionyl chloride and 3 drops of N,N-dimethylformamide were added, and stirred at 90° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in 5 ml of tetrahydrofuran. In a solution of 0.40 g of N-(2-pyridylmethyl) carbamic acid methyl ester in 5 ml of tetrahydrofuran, 0.27 g of t-butoxy potassium was added at room temperature with stirring, and stirred at the same temperature for 3 minutes. Then, the above-mentioned solution of acid chloride in tetrahydrofuran was added dropwise in the reaction mixture, after the completion of the addition dropwise, continued to stir at the same temperature for further 1 hour. After the completion of the reaction, the reaction mixture was diluted with 60 ml of ethyl acetate, washed with 50 ml of water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:2 to 1:1) to obtain 0.75 g of the aimed product as yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.56 (d, J=4.8 Hz, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.21 (s, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.58 (s, 3H), 2.40 (s, 3H).

Synthetic Example 29 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid amide (Compound of the present invention No. 5-066) Step 1: Production of 4-bromo-α-chloro-3-methylbenzaldoxime

In a solution of 82.0 g of 4-bromo-3-methylbenzaldoxime in 450 ml of tetrahydrofuran, 120.0 g of concentrated hydrochloric acid was added a dropwise with stirring under ice cooling over 45 minutes. Then, 220 ml of 8% sodium hypochlorite aqueous solution was carefully added dropwise over 75 minutes so that the temperature of the reaction mixture would not exceed 5° C., after the completion of the addition, continued to stir at 10° C. or less further for 90 minutes. After the completion of the reaction, nitrogen gas was blown through the reaction mixture for 45 minutes and precipitated insoluble material was filtered off, and tetrahydrofuran was distilled off under reduced pressure. The remaining aqueous solution was extracted with 240.0 g of ethyl acetate. The organic phase was washed with water (240 ml×2) and then insoluble material was filtered off, the solvent was distilled off under reduced pressure to obtain 93.5 g of the aimed product as pale yellow crystal.

Melting point 77.0 to 78.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.00 (bs, 1H), 7.71 (d, J=2.2 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.51 (dd, J=8.4, 2.2 Hz, 1H), 2.44 (s, 3H).

Step 2: Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 22.7 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene produced in Step 1 of Synthetic Example 3 and 26.0 g of 4-bromo-α-chloro-3-methylbenzaldoxime in 120 ml of tetrahydrofuran, 15.7 g of potassium hydrogen carbonate was added, and stirred under reflux with heat for 5 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off, then the solvent was distilled off under reduced pressure. 150 ml of water was added in the residue, stirred at room temperature for 18 hours, and precipitated crystal was filtered off and dried to obtain 38.6 g of the aimed product as white crystal.

Melting point 105.0 to 108.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.59 (d, J=8.4 Hz, 1H), 7.45-7.55 (m, 3H), 7.42 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.4, 2.1 Hz, 1H), 4.07 (d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.43 (s, 3H).

Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl chloride

In a solution of 18.1 g of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole and 3.94 g of sodium acetate in 42 ml of 1,2-dimethoxyethane and 42 ml of water in an autoclave, 0.42 g of triphenylphosphine and 0.09 g of palladium (II) acetate were added, and stirred under 1.5 MPa carbon monoxide atmosphere at 110° C. for 7 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, the solid was filtered off, then added in 100 ml of ethyl acetate. The organic phase was washed with 1% sodium hydrogen carbonate aqueous solution (70 ml×2), then with 1N hydrochloric acid (55 ml×2), dried with saturated sodium chloride aqueous solution and then the solvent was displaced by toluene. 2 drops of N,N-dimethylformamide was added in the resulting toluene solution, and 6.0 g of thionyl chloride was added dropwise with stirring at 80° C., and continued to stir at the same temperature further for 1.5 hour. After the completion of the reaction, insoluble material was filtered off, the solvent was distilled off under reduced pressure until the volume of the solvent was reduced to about one-third. Then, 50 ml of hexane was gradually added dropwise with stirring at 60° C., after the completion of the addition, left and cooled to room temperature with stirring, and continued to stir at room temperature further for 1 hour. Precipitated crystal was filtered off and dried to obtain 13.4 g of the aimed product as white crystal.

Melting point 140.5 to 143.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.25 (d, J=8.7 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.59 (s, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.60 (s, 3H).

Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid amide

In a mixture of 3.0 g of concentrated ammonia water and 15 ml of tetrahydrofuran, a solution of 3.0 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl chloride in 20 ml of tetrahydrofuran was added dropwise, after the completion of the addition, continued to stir further for 18 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 50 ml of ethyl acetate, washed with 50 ml of water, dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure to obtain 2.9 g of the aimed product as orange crystal.

Melting point 162.5 to 164.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.45-7.55 (m, 6H), 6.40 (bs, 1H), 6.00 (bs, 1H), 4.09 (d, J=17.0 Hz, 1H), 3.71 (d, J=17.0 Hz, 1H), 2.49 (s, 3H).

Synthetic Example 30 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide (Compound of the present invention No. 5-480) Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-hydroxymethyl)benzoic acid amide

In a solution of 7.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid amide synthesized in Synthetic Example 29 in 70 ml of 1,4-dioxane, 1.82 g of 37% formalin aqueous solution, 7.00 g of potassium carbonate and 15 ml of water were added, stirred at the same temperature for 3 hours. After the completion of the reaction, the reaction mixture was diluted by adding 200 ml of ethyl acetate, washed with water (50 ml×1) and then dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and filtered through silica gel, the solvent was distilled off under reduced pressure to obtain 7.00 g of crude aimed product as white crystal.

Melting point 69.0 to 73.0° C.

Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide

In a solution of 1.70 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(hydroxymethyl)benzoic acid amide in 20 ml of dichloromethane, 0.68 g of thionyl chloride was added with stirring at room temperature, stirred at the same temperature for 2 hours, then the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. In 0.33 g of 60% oily sodium hydride suspended in 30 ml of tetrahydrofuran, 1.50 g of 2,2,2-trifluoroethanol was added dropwise with stirring under ice cooling, and stirred at the same temperature for 10 minutes. Then, the solution of benzoic acid chloride in tetrahydrofuran prepared above was added dropwise in the reaction mixture with stirring under ice cooling, after the completion of the addition, continued to stir at room temperature for 1 hour. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with ethyl acetate (70 ml×1), and the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 1.20 g of the aimed product as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 6.64 (t, J=6.4 Hz, 1H), 5.02 (d, J=7.2 Hz, 2H), 4.05-4.15 (m, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.49 (s, 3H).

Synthetic Example 31 N-Carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide (Compound of the present invention No. 5-137)

In a solution of 0.37 g of glycine amide hydrochloride and 0.71 g of pyridine in 20 ml of dichloromethane, a solution of 1.31 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl chloride synthesized in Step 3 of Synthetic Example 29 in 10 ml of dichloromethane was added dropwise with stirring under ice cooling, after the completion of the addition, stirred at room temperature for 3 hours, then 3.00 g of triethyl amine was added in the reaction mixture, and continued to stir at the same temperature further for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, 50 ml of ethyl acetate and 50 ml of water were added in the residue, and the organic phase was collected, and the aqueous phase was further extracted with ethyl acetate (50 ml×2). The organic phases together were dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure, the residual solid was washed with hexane to obtain 1.24 g of the aimed product as white crystal.

Melting point 87.0 to 91.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.55 (m, 6H), 7.15-7.25 (m, 1H), 6.86 (s, 1H), 5.88 (s, 1H), 4.12 (d, J=5.1 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.74 (d, J=17.4 Hz, 1H), 2.49 (s, 3H).

Synthetic Example 32 N-Aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide hydrochloride (Compound of the present invention No. 5-507)

In a solution of 0.47 g of [bis(trifluoroacetoxy)iodo]benzene in 12 ml of acetonitrile-water (1:1), a solution of 0.47 g of N-carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide synthesized in Synthetic Example 31 was added with stirring at room temperature, and stirred at room temperature for 5 hours. After the completion of the reaction, 75 ml of water was added in the reaction mixture, 8 ml of concentrated hydrochloric acid was added, then washed with 100 ml of diethyl ether, and the organic phase was subjected to back extraction with 2N hydrochloric acid aqueous solution (20 ml×2). The aqueous phase was combined with the organic phase, water was distilled off, and the residual solid was washed with ethyl acetate to obtain 0.21 g of the aimed product as white crystal.

Melting point 155.0 to 157.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 9.0-9.1 (m, 1H), 7.4-7.7 (m, 8H), 4.64 (d, J=5.7 Hz, 2H), 4.16 (d, J=17.4 Hz, 1H), 3.80 (d, J=17.4 Hz, 1H), 2.50 (s, 3H).

Synthetic Example 33 N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoylaminomethyl]carbamic acid methyl ester (Compound of the present invention No. 5-515)

In a suspended solution of 0.13 g of N-aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide hydrochloride synthesized in Synthetic Example 32 in 4 ml of dichloromethane, 0.03 g of methyl chloroformate and 0.08 g of triethyl amine were added with stirring at room temperature, and stirred at room temperature for 3 hours. After the completion of the reaction, the solvent was distilled under reduced pressure, the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.06 g of the aimed product as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.35-7.55 (m, 6H), 7.17 (bs, 1H), 6.12 (bs, 1H), 4.73 (t, J=6.6 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.68 (s, 3H), 2.42 (s, 3H).

Synthetic Example 34 N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(2-tetrahydrofuranyl)benzoic acid amide (Compound of the present invention No. 5-494)

In a solution of 1.25 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl benzoic acid amide synthesized in Synthetic Example 29 and 0.32 g of 2,3-dihydrofuran in 30 ml of dichloromethane, 0.01 g of p-toluene sulfonic acid monohydrate was added with stirring at room temperature, and stirred at room temperature for 3 days. After the completion of the reaction, 30 ml of saturated sodium hydrogen carbonate aqueous solution was added in the reaction mixture, and extracted with ethyl acetate (30 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 1.18 g of the aimed product as colorless resinous substance.

Melting point 144.0 to 147.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.3-7.55 (m, 6H), 6.49 (d, J=8.1 Hz, 1H), 5.8-5.9 (m, 1H), 4.09 (d, J=17.1 Hz, 1H), 3.8-4.0 (m, 2H), 3.72 (d, J=17.1 Hz, 1H), 2.42 (s, 3H), 2.2-2.4 (m, 1H), 1.8-2.1 (m, 3H).

Synthetic Example 35 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methyl-N-(2-tetrahydrothienyl)benzoic acid amide (Compound of the present invention No. 6-133)

In a solution of 0.43 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-methyl benzoic acid amide synthesized similarly to Synthetic Example 29 and 0.20 g of triethylamine in 5 ml of toluene, 0.45 g of trimethyl silyl trifurate was added and stirred vigorously. 10 minutes after the stirring, the reaction mixture was cooled to 0° C., 0.10 g of tetrahydrothiophene-1-oxide and 0.06 g of zinc iodide were added with stirring, and continued to stir at room temperature further for 4 days. After the completion of the reaction, 10 ml of ice water was added in the reaction mixture, and extracted with ethyl acetate (20 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.09 g of the aimed product as white crystal.

Melting point 146.0 to 151.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.7 (m, 5H), 7.15-7.25 (m, 1H), 6.65-6.75 and 5.3-5.4 (m, 1H), 4.09 (d, J=17.1 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H), 3.12 and 2.77 (s, 3H), 2.85-3.15 (m, 2H), 2.33 and 2.30 (s, 3H), 1.7-2.3 (m, 4H).

Synthetic Example 36 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-ethenyl-2-methylbenzoic acid amide (Compound of the present invention No. 5-660)

In a solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-2-meth yl benzoic acid amide synthesized in Synthetic Example 29, 0.865 g of ethyl vinyl ether and 0.022 g of 1,10-phenanthroline in 10 ml of 1,2-dimethoxyethane, 0.04 g of bis(trifluoroacetoxy)palladium (II) was added and stirred at room temperature for 19 hours. After the completion of the reaction, 30 ml of water was added in the reaction mixture, and extracted with ethyl acetate (40 ml×1), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, then filtered through silica gel, and the solvent was distilled under reduced pressure to obtain 0.45 g of the aimed product as pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.3-7.6 (m, 7H), 7.05-7.25 (m, 1H), 4.75 (d, J=15.6 Hz, 1H), 4.57 (d, J=8.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.1 Hz, 1H), 2.50 (s, 3H).

Synthetic Example 37 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzhydroxamic acid N-(2,2,2-trifluoroethyl) carbamic acid anhydride (Compound of the present invention No. 5-663)

In a solution of 0.30 g of hydroxylamine hydrochloride in 10 ml of methanol, a solution of 0.65 g of potassium hydroxide in 5 ml of methanol was added, then a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoic acid methyl ester synthesized similarly to Steps 1 to 4 of Synthetic Example 28 in 10 ml of methanol was added, and stirred at 40° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of acetic acid aqueous solution (1:1) was added in the residue, and extracted with ethyl acetate (20 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. Toluene was added in the residue and the remaining acetic acid was distilled off azeotropically to obtain 1.01 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzhydroxamic acid as white crystal.

In a solution of 0.16 g of carbonyl diimidazole in 2 ml of tetrahydrofuran, 0.10 g of 2,2,2-trifluoroethylamine was added, and stirred at room temperature for 1 hour. Then, a solution of 0.10 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzhydroxamic acid in 2 ml of tetrahydrofuran was added in the reaction mixture, and continued to stir at room temperature further for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of water was added in the residue, and extracted with ethyl acetate (10 ml×1). The organic phase was washed with 5 ml of 2N hydrochloric acid aqueous solution, dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel thin-layer chromatography (Kanto Chemical Co., Ltd.: PLC plates silica gel 60 F254 20×20 cm layer thickness 2 mm) that was developed with ethyl acetate-hexane (1:1) to obtain 0.12 g of the aimed product as white crystal.

Melting point 111.0 to 114.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 9.08 (bs, 1H), 7.4-7.6 (m, 6H), 6.07 (bs, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.8-3.95 (m, 2H), 3.70 (d, J=17.4 Hz, 1H), 2.56 (s, 3H).

The compounds of the present invention can be produced according to the above-mentioned production methods and working examples. The examples of the compounds produced similarly to Synthetic Examples 1 to 37 are shown in Tables 7 to 20 to which the present invention is not limited. In the meantime, in Tables, the indication “Et” means ethyl, hereinafter similarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and “Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and “Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu” and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu” and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” means normal pentyl, c-Pen” and “Pen-c” mean cyclopentyl, “n-Hex” and “Hex-n” mean normal hexyl, “c-Hex” and “Hex-c” mean cyclohexyl, “Ph” means phenyl, “TMS” means trimethylsilyl, “-Q1” means hydrochloride, “-Q2” means p-toluenesulfonate, “-Q3” means fumarate, “-Q4” means maleate, “-Q5” means triethylamine salt, and in Tables, aromatic heterocyclic rings of D-1a to D-54b are the following structures, respectively.

in Tables, saturated heterocyclic rings of E-4-a to E-43a are the following structures, respectively.

In Tables, partially saturated heterocyclic ring of M-5a is the following structure

In Tables, T-4 to T-51 are the following structures, respectively

In addition, in Tables, the number showing the substitution position of substituents (X)_(m) and (Y)_(n) correspond to the position number indicated in the following structural formulae. The indication “−” means no-substitution.

Further, in Tables, the indication of “Mw” shows the calculated value of molecular weight, the indication of “M⁺+H” shows the measured value of molecular ion peak, and “*1”, “*2” or “*3” means “resinous”, “oily” or “decomposition”, respectively.

TABLE 7

No. (X)_(m) R³ R¹ Mw M⁺ + H 1-001 — C(O)OCH₃ CH₂CF₃ 406.36 407.00 1-002 — C(O)OCH₃ CH₂Ph 414.46 415.07 1-003 2-F C(O)OCH₃ CH₂CF₃ 424.35 424.99 1-004 2-Cl C(O)OCH₃ CH₂CF₃ 440.81 440.94 1-005 3-Br CF₃ CH₂Ph 503.31 502.75 1-006 4-Br CF₃ CH₂CF₃ 495.21 494.68 1-007 4-Br CF₃ CH₂Ph 503.31 502.74 1-008 3-CH₃ CF₃ CH₂CF₃ 430.34 430.91 1-009 3-CH₃ CF₃ CH₂Ph 438.44 438.95 1-010 4-CH₃ CF₃ CH₂CF₃ 430.34 430.92 1-011 4-CH₃ CF₃ CH₂Ph 438.44 438.91 1-012 4-Bu-t CF₃ CH₂CF₃ 472.42 472.94 1-013 4-Bu-t CF₃ CH₂Ph 480.52 480.99 1-014 2-CF₃ C(O)OCH₃ CH₂CF₃ 474.36 474.87 1-015 3-CF₃ CF₃ CH₂CF₃ 484.32 484.78 1-016 3-CF₃ CF₃ CH₂Ph 492.41 492.82 1-017 4-CF₃ CF₃ CH₂CF₃ 484.32 484.80 1-018 4-CF₃ CF₃ CH₂Ph 492.41 492.85 1-019 2-OCH₃ C(O)OCH₃ CH₂CF₃ 436.39 436.99 1-020 3-OCH₃ CF₃ CH₂CF₃ 446.34 446.89 1-021 3-OCH₃ CF₃ CH₂Ph 454.44 454.94 1-022 4-OCH₃ CF₃ CH₂CF₃ 446.34 446.89 1-023 4-OCH₃ CF₃ CH₂Ph 454.44 454.91 1-024 4-OCH₃ C(O)OCH₃ CH₂CF₃ 436.39 437.00 1-025 3-OCF₃ CF₃ CH₂CF₃ 500.31 500.76 1-026 3-OCF₃ CF₃ CH₂Ph 508.41 508.80 1-027 4-OCF₃ CF₃ CH₂CF₃ 500.31 500.76 1-028 4-OCF₃ CF₃ CH₂Ph 508.41 508.82 1-029 4-OPh CF₃ CH₂CF₃ 508.41 508.85 1-030 4-OPh CF₃ CH₂Ph 516.51 516.88 1-031 4-SCH₃ CF₃ CH₂CF₃ 462.41 462.84 1-032 4-SCH₃ CF₃ CH₂Ph 470.51 470.88 1-033 4-SO₂CH₃ CF₃ CH₂CF₃ 494.41 494.86 1-034 3-NHC(O)OH₃ CF₃ CH₂CF₃ 473.37 473.90 1-035 3-NHC(O)OH₃ CF₃ CH₂Ph 481.47 481.93 1-036 4-NHC(O)OH₃ CF₃ CH₂CF₃ 473.37 473.81 1-037 4-NHC(O)OH₃ CF₃ CH₂Ph 481.47 481.94 1-038 4-N(CH₃)₂ CF₃ CH₂CF₃ 459.38 459.90 1-039 4-N(CH₃)₂ CF₃ CH₂Ph 467.48 467.94 1-040 3-NO₂ CF₃ CH₂CF₃ 461.31 461.82 1-041 3-NO₂ CF₃ CH₂Ph 469.41 469.86 1-042 3-TMS CF₃ CH₂CF₃ 488.50 488.87 1-043 3-CN CF₃ CH₂Ph 449.42 449.89 1-044 4-CN CF₃ CH₂Ph 449.42 449.89 1-045 3-CHO CF₃ CH₂CF₃ 444.33 444.89 1-046 3-C(O)CH₃ CF₃ CH₂CF₃ 458.35 458.82 1-047 3-C(O)CH₃ CF₃ CH₂Ph 466.45 466.81 1-048 4-C(O)OH₃ CF₃ CH₂CF₃ 458.35 458.80 1-049 4-C(O)CH₃ CF₃ CH₂Ph 466.45 466.86 1-050 3-C(O)OEt CF₃ CH₂CF₃ 488.38 488.89 1-051 3-C(O)OEt CF₃ CH₂Ph 496.48 496.92 1-052 4-Ph CF₃ CH₂CF₃ 492.41 492.81 1-053 3,4-F2 CF₃ CH₂Pr-c 424.36 424.91 1-054 3,4-F2 CF₃ CH₂Ph 460.40 460.87 1-055 3,5-F2 CF₃ CH₂CF₃ 452.30 452.84 1-056 3,5-F2 CF₃ CH₂Ph 460.40 460.89 1-057 3-Cl-4-F CF₃ CH₂CF₃ 468.75 468.76 1-058 3-Cl-4-F CF₃ CH₂Ph 476.85 476.80 1-059 2,5-Cl₂ CF₃ CH₂CF₃ 485.21 484.79 1-060 2,5-Cl₂ CF₃ CH₂Ph 493.30 492.82 1-061 2,5-Cl₂ CF₃ CH₂(D-47a) 494.29 493.84 1-062 3,4-Cl₂ CF₃ Et 431.24 430.93 1-063 3,4-Cl₂ CF₃ n-Pr 445.27 444.94 1-064 3,4-Cl₂ CF₃ i-Pr 445.27 444.94 1-065 3,4-Cl₂ CF₃ n-Bu 459.29 458.97 1-066 3,4-Cl₂ CF₃ CH₂Pr-c 457.28 456.94 1-067 3,4-Cl₂ CF₃ s-Bu 459.29 458.93 1-068 3,4-Cl₂ CF₃ t-Bu 459.29 458.92 1-069 3,4-Cl₂ CF₃ c-Bu 457.27 456.79 1-070 3,4-Cl₂ CF₃ n-Pen 473.32 473.02 1-071 3,4-Cl₂ CF₃ CH₂Bu-s 473.32 472.82 1-072 3,4-Cl₂ CF₃ CH₂Bu-t 473.32 472.94 1-073 3,4-Cl₂ CF₃ CH(CH₃)Pr-n 473.32 472.94 1-074 3,4-Cl₂ CF₃ c-Pen 471.31 470.99 1-075 3,4-Cl₂ CF₃ n-Hex 487.35 486.96 1-076 3,4-Cl₂ CF₃ c-Hex 485.33 484.93 1-077 3,4-Cl₂ CF₃ CH₂Hex-c 499.35 498.88 1-078 3,4-Cl₂ CF₃ CH₂(T-39) 539.42 538.88 1-079 3,4-Cl₂ CF₃ CH₂CH₂Cl 465.69 464.73 1-080 3,4-Cl₂ CF₃ CH₂CF₃ 485.21 484.85 1-081 3,4-Cl₂ CF₃ CH₂CF₂CF₂CF₃ 585.23 584.65 1-082 3,4-Cl₂ CF₃ CH₂CH(CH₃)OH(R) 461.26 460.78 1-083 3,4-Cl₂ CF₃ CH₂CH(CH₃)OH(S) 461.26 460.82 1-084 3,4-Cl₂ CF₃ CH₂CH(CH₃)OC(O)NHEt(S) 532.34 531.78 1-085 3,4-Cl₂ CF₃ CH(CH₃)CH₂OCH₃ 475.29 474.94 1-086 3,4-Cl₂ CF₃ CH₂CH(Et)OH 475.29 474.82 1-087 3,4-Cl₂ CF₃ CH(Et)CH₂OCH₃ 489.32 488.95 1-088 3,4-Cl₂ CF₃ CH₂OH(OCH₃)₂ 491.29 490.80 1-089 3,4-Cl₂ CF₃ CH₂CH₂CH₂OH 461.27 460.97 1-090 3,4-Cl₂ CF₃ CH₂CH₂CH₂OCH₃ 475.29 474.98 1-091 3,4-Cl₂ CF₃ CH₂(T-13) 515.35 514.80 1-092 3,4-Cl₂ CF₃ CH₂(E-11c) 517.33 516.79 1-093 3,4-Cl₂ CF₃ CH₂CH₂SCH₃ 477.33 476.75 1-094 3,4-Cl₂ CF₃ CH₂CH₂SBu-t 519.41 518.96 1-095 3,4-Cl₂ CF₃ CH₂CH₂CH₂SCH₃ 491.35 490.92 1-096 3,4-Cl₂ CF₃ CH₂CH₂NHC(O)OBu-t 546.37 545.75 1-097 3,4-Cl₂ CF₃ CH₂CH₂CH₂Si(OCH₃)3 565.44 564.77 1-098 3,4-Cl₂ CF₃ CH₂CH₂CH₂Si(CH₃)(OEt)₂ 577.49 576.79 1-099 3,4-Cl₂ CF₃ CH₂C(O)OCH₃ 475.25 474.89 1-100 3,4-Cl₂ CF₃ CH₂CH₂C(O)OCH₃ 489.28 488.80 1-101 3,4-Cl₂ CF₃ CH₂C(O)NH₂ 460.24 459.74 1-102 3,4-Cl₂ CF₃ CH₂OH═CH₂ 443.25 442.81 1-103 3,4-Cl₂ CF₃ CH₂CH₂(T-17) 511.36 510.76 1-104 3,4-Cl₂ CF₃ CH₂C≡CH 441.24 440.91 1-105 3,4-Cl₂ CF₃ CH₂Ph 493.31 492.86 1-106 3,4-Cl₂ CF₃ CH₂(Ph-2-F) 511.30 510.80 1-107 3,4-Cl₂ CF₃ CH₂(Ph-3-F) 511.30 510.81 1-108 3,4-Cl₂ CF₃ CH₂(Ph-2-Cl) 527.75 526.74 1-109 3,4-Cl₂ CF₃ CH₂(Ph-3-Cl) 527.75 526.75 1-110 3,4-Cl₂ CF₃ CH₂(Ph-2-CH₃) 507.33 506.78 1-111 3,4-Cl₂ CF₃ CH₂(Ph-4-CH₃) 507.33 506.73 1-112 3,4-Cl₂ CF₃ CH₂(Ph-4-Bu-t) 549.41 548.77 1-113 3,4-Cl₂ CF₃ CH₂(Ph-2-CF₃) 561.30 560.72 1-114 3,4-Cl₂ CF₃ CH₂(Ph-3-CF₃) 561.30 560.69 1-115 3,4-Cl₂ CF₃ CH₂(Ph-4-CF₃) 561.30 560.97 1-116 3,4-Cl₂ CF₃ CH₂(Ph-2-OCH₃) 523.33 522.77 1-117 3,4-Cl₂ CF₃ CH₂(Ph-3-OCH₃) 523.33 522.74 1-118 3,4-Cl₂ CF₃ CH₂(Ph-4-OCH₃) 523.33 522.68 1-119 3,4-Cl₂ CF₃ CH₂(Ph-3-0CF₃) 577.30 576.69 1-120 3,4-Cl₂ CF₃ CH₂(Ph-4-SO₂CH₃) 571.40 570.71 1-121 3,4-Cl₂ CF₃ CH₂[Ph-4-N(CH₃)₂] 536.37 535.81 1-122 3,4-Cl₂ CF₃ CH₂(Ph-3-NO₂) 538.30 537.64 1-123 3,4-Cl₂ CF₃ CH₂(Ph-4-NO₂) 538.30 537.66 1-124 3,4-Cl₂ CF₃ CH₂[Ph-4-C(O)OCH₃] 551.34 550.74 1-125 3,4-Cl₂ CF₃ CH₂(Ph-2,5-F₂) 529.29 528.72 1-126 3,4-Cl₂ CF₃ CH₂(Ph-2,6-F₂) 529.29 528.81 1-127 3,4-Cl₂ CF₃ CH₂(Ph-3,5-F₂) 529.29 528.73 1-128 3,4-Cl₂ CF₃ CH₂(Ph-3-Cl-4-F) 545.74 544.67 1-129 3,4-Cl₂ CF₃ CH₂(Ph-2,3-Cl₂) 562.20 560.72 1-130 3,4-Cl₂ CF₃ CH₂(Ph-2,4-Cl₂) 562.20 560.72 1-131 3,4-Cl₂ CF₃ CH₂(Ph-2,5-Cl₂) 562.20 560.72 1-132 3,4-Cl₂ CF₃ CH₂(Ph-2,6-Cl₂) 562.20 560.73 1-133 3,4-Cl₂ CF₃ CH₂(Ph-3,5-Cl₂) 562.20 560.64 1-134 3,4-Cl₂ CF₃ CH₂(Ph-3-CF₃-4-F) 579.29 578.70 1-135 3,4-Cl₂ CF₃ CH₂[Ph-3,4-(OCH₃)₂] 553.36 552.76 1-136 3,4-Cl₂ CF₃ CH₂(Ph-3-OCH₂O-4) 537.31 536.73 1-137 3,4-Cl₂ CF₃ CH₂(1-Naph) 543.36 542.80 1-138 3,4-Cl₂ CF₃ CH(CH₃)Ph 507.34 506.88 1-139 3,4-Cl₂ CF₃ CH(CH₃)(Ph-3-Cl) 541.78 540.70 1-140 3,4-Cl₂ CF₃ C(CH₃)₂Ph 521.37 520.99 1-141 3,4-Cl₂ CF₃ CH₂CH₂Ph 507.34 507.01 1-142 3,4-Cl₂ CF₃ CH₂CH₂(Ph-4-OPh) 599.44 598.95 1-143 3,4-Cl₂ CF₃ CH₂OH(CH₃)Ph 521.37 520.93 1-144 3,4-Cl₂ CF₃ CH₂CHPh₂ 583.43 582.79 1-145 3,4-Cl₂ CF₃ CH(CH₃)CH₂(Ph-4-Cl) 555.81 554.78 1-146 3,4-Cl₂ CF₃ T-9 519.35 518.88 1-147 3,4-Cl₂ CF₃ CH₂CH₂CH₂Ph 521.37 520.97 1-148 3,4-Cl₂ CF₃ CH₂CH₂SCH₂Ph 553.43 552.75 1-149 3,4-Cl₂ CF₃ CH₂C(O)(Ph-4-OCH₃) 551.34 550.66 1-150 3,4-Cl₂ CF₃ CH₂(D-1c)CH₃ 497.29 496.80 1-151 3,4-Cl₂ CF₃ CH₂(D-3a) 499.33 498.70 1-152 3,4-Cl₂ CF₃ CH₂(D-3b)CH₃ 513.36 512.74 1-153 3,4-Cl₂ CF₃ CH₂(D-47a) 494.29 493.84 1-154 3,4-Cl₂ CF₃ CH₂(D-47f) 596.74 595.79 1-155 3,4-Cl₂ CF₃ CH₂(D-48a) 494.29 493.84 1-156 3,4-Cl₂ CF₃ CH₂(D-49a) 494.29 493.86 1-157 3,4-Cl₂ CF₃ CH₂(D-53b)CH₃ 509.31 508.78 1-158 3,4-Cl₂ CF₃ CH₂CH₂(D-3a) 513.36 512.71 1-159 3,4-Cl₂ CF₃ CH₂CH₂(D-47a) 508.32 507.76 1-160 3,4-Cl₂ CF₃ CH₂CH₂(D-48a) 508.32 507.77 1-161 3,4-Cl₂ CF₃ CH₂CH₂CH₂(D-24a) 511.32 510.84 1-162 3,4-Cl₂ CF₃ T-21 472.24 471.77 1-163 3,4-Cl₂ CF₃ T-22 488.31 487.72 1-164 3,4-Cl₂ CF₃ (D-8b)CH₃ 484.25 483.75 1-165 3,4-Cl₂ CF₃ D-11c 581.35 580.66 1-166 3,4-Cl₂ CF₃ D-21a 486.29 485.70 1-167 3,4-Cl₂ CF₃ (D-21b)CH₃ 500.32 499.70 1-168 3,4-Cl₂ CF₃ (D-21c)CH₃ 500.32 499.70 1-169 3,4-Cl₂ CF₃ (D-21c)NO₂ 531.29 530.60 1-170 3,4-Cl₂ CF₃ D-25d 533.33 532.73 1-171 3,4-Cl₂ CF₃ D-48a 480.27 479.76 1-172 3,4-Cl₂ CF₃ D-49a 480.27 479.76 1-173 3,4-Cl₂ CF₃ OPr-n 461.27 460.94 1-174 3,4-Cl₂ CF₃ N(CH₃)₂ 446.26 445.92 1-175 3,5-Cl₂ CF₃ CH₂Pr-c 457.27 456.83 1-176 3,5-Cl₂ CF₃ CH₂CH₂CF₃ 499.23 498.79 1-177 3,5-Cl₂ CF₃ CH₂CH₂OEt 475.29 474.86 1-178 3,5-Cl₂ CF₃ CH₂CH₂OCH₂CH₂OH 491.29 490.78 1-179 3,5-Cl₂ CF₃ CH₂CH(CH₃)OH 461.27 460.88 1-180 3,5-Cl₂ CF₃ CH₂CH₂CH₂OEt 489.31 488.90 1-181 3,5-Cl₂ CF₃ CH₂CH₂CH₂OPr-i 503.34 502.86 1-182 3,5-Cl₂ CF₃ CH₂CH₂SEt 491.35 490.99 1-183 3,5-Cl₂ CF₃ CH₂(Ph-3-Br) 572.20 570.68 1-184 3,5-Cl₂ CF₃ CH₂(Ph-3-OCH₃) 523.33 522.80 1-185 3,5-Cl₂ CF₃ CH₂(Ph-4-OCH₃) 523.33 522.74 1-186 3,5-Cl₂ CF₃ CH₂(Ph-4-OCF₃) 577.30 576.75 1-187 3,5-Cl₂ CF₃ CH₂(Ph-4-SO₂NH₂₎ 572.38 571.78 1-188 3,5-Cl₂ CF₃ CH₂(Ph-3-NO₂) 538.30 537.76 1-189 3,5-Cl₂ CF₃ CH₂(Ph-4-NO₂) 538.30 537.76 1-190 3,5-Cl₂ CF₃ CH₂CH₂(Ph-3-Cl) 541.78 540.71 1-191 3,5-Cl₂ CF₃ CH₂CH₂(Ph-4-OCH₃) 537.36 536.79 1-192 3,5-Cl₂ CF₃ CH₂CH₂(Ph-3,4-Cl₂) 576.22 574.60 1-193 3,5-Cl₂ CF₃ CH₂CH₂[Ph-3,4-(OCH₃)₂] 567.38 566.77 1-194 3,5-Cl₂ CF₃ CH₂CH₂OPh 523.33 522.85 1-195 3,5-Cl₂ CF₃ Ph-4-OCH₃ 509.30 508.75 1-196 3,5-Cl₂ CF₃ (D-21b)CH₂C(O)OEt 572.38 571.70 1-197 3,5-Cl₂ CF₃ (D-21c)Br 565.19 563.59 1-198 3,5-Cl₂ CF₃ (D-21c)SO₂(Ph-4-NO₂) 671.45 670.55 1-199 3,5-Cl₂ CF₃ D-21d 514.35 513.72 1-200 3,5-Cl₂ CF₃ D-21e 536.35 535.70 1-201 3,5-Cl₂ CF₃ D-21f 570.80 569.68 1-202 3,5-Cl₂ CF₃ D-21g 570.80 569.68 1-203 3,5-Cl₂ CF₃ D-21h 566.38 565.71 1-204 3,5-Cl₂ CF₃ D-21i 566.38 565.76 1-205 3,5-Cl₂ CF₃ D-21j 581.35 580.69 1-206 3,5-Cl₂ CF₃ NHPh 494.29 493.81 1-207 3,5-Br₂ CF₃ CH₂CF₃ 574.11 572.49 1-208 3,5-Br₂ CF₃ CH₂Ph 582.21 580.61 1-209 3-CH₃-4-F CF₃ CH₂Ph 456.43 456.87 1-210 3,4-(CH₃)₂ CF₃ CH₂CF₃ 444.37 444.89 1-211 3,4-(CH₃)₂ CF₃ CH₂Ph 452.47 452.94 1-212 3,5-(CH₃)₂ CF₃ CH₂CF₃ 444.37 444.86 1-213 3,5-(CH₃)₂ CF₃ CH₂Ph 452.47 452.95 1-214 3,5-(CF₃)₂ CF₃ CH₂CF₃ 552.31 552.72 1-215 3,5-(CF₃)₂ CF₃ CH₂Ph 560.41 560.76 1-216 3-OEt-4-Cl CF₃ CH₂CF₃ 494.81 494.76 1-217 3-OEt-4-Cl CF₃ CH₂Ph 502.91 502.81 1-218 3,4-(OCH₃)₂ CF₃ CH₂CF₃ 476.37 476.83 1-219 3,4-(OCH₃)₂ CF₃ CH₂Ph 484.47 484.90 1-220 3-OCH₂O-4 CF₃ CH₂Pr-c 432.39 432.89 1-221 3-OCH₂O-4 CF₃ CH₂Ph 468.42 468.86 1-222 3,5-(CHO)₂ CF₃ CH₂CF₃ 472.34 472.92 1-223 3-CH═CHCH═CH-4 CF₃ CH₂CF₃ 466.38 466.83 1-224 3-CH═CHCH═CH-4 CF₃ CH₂Ph 474.47 474.86 1-225 3,4,5-F₃ CF₃ CH₂CF₃ 470.29 470.77 1-226 3,4,5-F₃ CF₃ CH₂Ph 478.39 478.82

TABLE 8

No. (X)_(m) (Y)_(n) R² R¹ Mw M⁺ + H 2-001 3,4-F₂ — CH₃ CH₂Ph 474.42 474.88 2-002 3,4-Cl₂ — CH₃ CH3 431.24 430.91 2-003 3,4-Cl₂ — Et Et 459.29 458.94 2-004 3,4-Cl₂ — CH₃ n-Bu 473.32 472.97 2-005 3,4-Cl₂ — CH₃ i-Bu 473.32 472.89 2-006 3,4-Cl₂ — —CH₂CH₂CH₂CH₂— 457.28 456.85 2-007 3,4-Cl₂ — —CH₂CH₂CH₂CH₂CH₂— 471.31 470.84 2-008 3,4-Cl₂ — —CH₂CH₂CH₂CH₂CH(CH₃)— 485.33 484.83 2-009 3,4-Cl₂ — —CH₂CH₂CH₂CH(CH₃)CH₂— 485.33 484.82 2-010 3,4-Cl₂ — —CH₂CH(CH₃)CH₂CH(CH₃)CH₂— 499.35 498.82 2-011 3,4-Cl₂ — —CH₂CH₂OCH₂CH₂— 473.28 472.75 2-012 3,4-Cl₂ — —CH₂CH(CH₃)OCH(CH₃)CH₂— 501.33 500.77 2-013 3,4-Cl₂ — —CH₂CH₂SCH₂CH₂— 489.34 488.74 2-014 3,4-Cl₂ — —CH₂CH₂N(CHO)CH₂CH₂— 500.30 499.76 2-015 3,4-Cl₂ — CH₃ CH₂CH═CH₂ 457.27 456.87 2-016 3,4-Cl₂ — CH₂CH═CH₂ CH₂CH═CH₂ 483.31 482.85 2-017 3,4-Cl₂ — CH₃ CH₂C≡CH 455.26 454.86 2-018 3,4-Cl₂ — CH₃ CH₂Ph 507.34 506.93 2-019 3,4-Cl₂ — Et CH₂(D-48e)Cl 556.79 555.73 2-020 3,5-Cl₂ — Et Et 459.29 458.85 2-021 3,5-Cl₂ — CH₃ CH₂Ph 507.33 506.79 2-022 3,5-Cl₂ — Et CH₂Ph 521.36 520.79 2-023 3,5-Cl₂ — CH₂Ph CH₂Ph 583.43 582.79 2-024 3,5-Cl₂ 2-CH₃ H CH₂CH₂OH 461.26 460.99 2-025 3,5-Cl₂ 2-CH₃ H CH₂CH₂OPr-n 503.34 502.99 2-026 3,5-Cl₂ 2-CH₃ H CH₂CH₂OPr-i 503.34 502.98 2-027 3,5-Cl₂ 2-CH₃ H CH₂CH₂OCH₂CH₂OH 505.31 504.95 2-028 3,5-Cl₂ 2-CH₃ H CH₂CH₂OPh 537.36 536.94 2-029 3,5-Cl₂ 2-CH₃ H CH(CH₃)CH₂OCH₃ 489.31 488.98 2-030 3,5-Cl₂ 2-CH₃ H CH₂CH₂N(CH₃)₂ 488.33 487.98 2-031 3,5-Cl₂ 2-CH₃ H CH(Ph)C(O)OCH₃(R) 565.37 564.84 2-032 3,5-Cl₂ 2-CH₃ H CH(Ph)C(O)OCH₃(S) 565.37 564.92 2-033 3,5-Cl₂ 2-CH₃ H CH₂CH₂C(O)OCH₃ 503.30 502.91 2-034 3,5-Cl₂ 2-CH₃ H CH₂(Ph-4-OCH₃) 537.36 536.98 2-035 3,5-Cl₂ 2-CH₃ H CH₂(Ph-4-CN) 532.34 531.94 2-036 3,5-Cl₂ 2-CH₃ H CH₂CH₂(D-47a) 522.35 521.94 2-037 3,5-Cl₂ 2-CH₃ H T-29b 562.32 559.80* 2-038 3,5-Cl₂ 2-CH₃ H NHCH₂C(O)OEt 518.31 517.93 2-039 3,5-Cl₂ 2-CH₃ H NHCHO 460.23 457.86* 2-040 3,5-Cl₂ 2-CH₃ H NHC(O)CH₂(D-3a) 556.38 553.71* 2-041 3,5-Cl₂ 2-CH₃ H N(CH₃)C(S)NH₂ 505.34 504.82 2-042 3,5-Cl₂ 2-CH₃ H N(CH₃)C(S)NHCH₃ 519.37 518.88 2-043 3,5-Cl₂ 2-CH₃ H T-40 530.37 529.98 2-044 3,5-Cl₂ 2-CH₃ H NH(Ph-2-F) 526.31 525.92 2-045 3,5-Cl₂ 2-CH₃ H NH(Ph-3-F) 526.31 525.92 2-046 3,5-Cl₂ 2-CH₃ H NH(Ph-4-F) 526.31 523.89* 2-047 3,5-Cl₂ 2-CH₃ H NH(Ph-4-Br) 587.22 585.91 2-048 3,5-Cl₂ 2-CH₃ H NH(Ph-4-CH₃) 522.35 521.93 2-049 3,5-Cl₂ 2-CH₃ H NH(Ph-4-Pr-i) 550.40 549.94 2-050 3,5-Cl₂ 2-CH₃ H NH(Ph-4-OCF₃) 592.32 591.97 2-051 3,5-Cl₂ 2-CH₃ H NH(Ph-4-CN) 533.33 533.01 2-052 3,5-Cl₂ 2-CH₃ H N(CH₃)(D-47d)CF₃ 591.33 590.99 2-053 3,5-Cl₂ 2-CH₃ H N═CHC(CH₃)═CHPh 560.39 559.95 2-054 3,5-Cl₂ 2-CH₃ H D-47a 494.29 493.94 2-055 3,5-Cl₂ 2-CH₃ H D-49a 494.29 493.97 2-056 3-OCH₂O-4 — CH₃ CH₂Ph 482.45 482.86 2-057 3,5-Cl₂ 2-CH₃ C(O)OCH₃CH₂CH═CH₂ 515.31 514.97 2-058 3,5-Cl₂ 2-CH₃ C(O)OPr-i CH₂CH═CH₂ 543.36 541.04* 2-059 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CH₂Cl 523.72 522.84 2-060 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CHCl₂ 558.16 554.92* 2-061 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CCl₃ 592.61 588.88* 2-062 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CH₂CF₃ 557.27 557.03 2-063 3,5-Cl₂ 2-CH₃ H C(O)OCH(CH₂Cl)₂ 572.19 570.94* 2-064 3,5-Cl₂ 2-CH₃ H C(O)OCH(CF₃)₂ 611.24 608.86* 2-065 3,5-Cl₂ 2-CH₃ H C(O)OCH(CH₃)CHClCH₃ 551.77 548.95* 2-066 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CH₂CH₂CH₂Cl 551.77 550.99 2-067 3,5-Cl₂ 2-CH₃ H C(O)OCH₂C(CF₃)₂CH₃ 639.29 636.95* 2-068 3,5-Cl₂ 2-CH₃ H T-25 501.33 502.05 2-069 3,5-Cl₂ 2-CH₃ H (D-21c)C(O)OEt 571.38 572.04 In Table above, the indication of “*” shows the measured value of molecular ion peak of M + H measured with negative mode.

TABLE 9

No. (X)_(m) R³ R¹ m.p. (° C.) 3-001 — CF₃ CH₂CF₃ 172.0-173.0 3-002 3-Cl CF₃ CH₂CF₃ 157.0-158.0 3-003 3-Cl CF₃ CH₂Ph 168.0-169.0 3-004 4-Cl CF₃ CH₂CF₃ 190.0-191.0 3-005 4-Cl CF₃ CH₂Ph 212.0-214.0 3-006 3-Br CF₃ CH₂CF₃ 132.0-135.0 3-007 3-OCF₃ CF₃ CH₂(D-47a) 145.0-147.0 3-008 3-OCH₂Ph CF₃ CH₂CF₃ 146.0-149.0 3-009 3-OCH₂(Ph-2-Cl) CF₃ CH₂CF₃ 158.0-159.0 3-010 3-OCH₂(Ph-2-Cl) CF₃ CH₂(D-47a) *1 3-011 3-SEt CF₃ CH₂CF₃ 105.0-106.0 3-012 3-CN CF₃ CH₂CF₃ 93.0-96.0 3-013 4-CN CF₃ CH₂CF₃ 149.0-151.0 3-014 3-CH═NOH CF₃ CH₂CF₃ 168.0-169.0 3-015 3-CH═NOCH₃ CF₃ CH₂CF₃ *1 3-016 4-C(CH₃)═NOCH₃(E) CF₃ CH₂CF₃ 160.0-162.0 3-017 4-C(CH₃)═NOCH₃(Z) CF₃ CH₂CF₃ *1 3-018 3,4-F₂ CF₃ CH₂CF₃ 150.0-152.0 3-019 2,4-Cl₂ CF₃ CH₂CF₃ 149.0-151.0 3-020 3,4-Cl₂ H CH₂CF₃ 161.0-162.0 3-021 3,4-Cl₂ H CH₂Ph 147.0-148.0 3-022 3,4-Cl₂ CH₃ CH₂Pr-c 157.0-158.0 3-023 3,4-Cl₂ CH₃ CH₂CF₃ 120.0-122.0 3-024 3,4-Cl₂ CH₃ CH₂Ph 153.0-155.0 3-025 3,4-Cl₂ CF₃ CH₃ 139.0-140.0 3-026 3,4-Cl₂ CF₃ c-Pr 193.0-194.0 3-027 3,4-Cl₂ CF₃ i-Bu 158.0-159.0 3-028 3,4-Cl₂ CF₃ CH₂Bu-c 177.0-179.0 3-029 3,4-Cl₂ CF₃ CH₂CH(Et)Bu-n 125.0-127.0 3-030 3,4-Cl₂ CF₃ CH₂CF₂CF₃ 171.0-173.0 3-031 3,4-Cl₂ CF₃ CH₂(E-4a) 136.0-138.0 3-032 3,4-Cl₂ CF₃ CH(CH₃)CH₂SCH₃ 145.0-147. 3-033 3,4-Cl₂ CF₃ C(CH₃)₂CH₂SCH₃ 150.0-152.0 3-034 3,4-Cl₂ CF₃ C(CH₃)₂CH₂S(O)CH₃ *1 3-035 3,4-Cl₂ CF₃ C(CH₃)₂CH₂SO₂CH₃ 161.0-163.0 3-036 3,4-Cl₂ CF₃ CH₂CH₂CH₂C(O)OEt 105.0-107.0 3-037 3,4-Cl₂ CF₃ CH₂(Ph-4-F) 155.0-156.0 3-038 3,4-Cl₂ CF₃ CH₂(Ph-4-Cl) 191.0-193.0 3-039 3,4-Cl₂ CF₃ CH₂(Ph-3-CH₃) 198.0-200.0 3-040 3,4-Cl₂ CF₃ CH₂(Ph-3,4-Cl₂) 161.0-162.0 3-041 3,4-Cl₂ CF₃ CH₂CH(Ph)OH 211.0-213.0 3-042 3,4-Cl₂ CF₃ CH₂C(O)(Ph-4-Br) 193.0-195.0 3-043 3,4-Cl₂ CF₃ CH₂(D-1a) 179.0-180.0 3-044 3,4-Cl₂ CF₃ CH₂(D-48e)Cl 154.0-157.0 3-045 3,4-Cl₂ CF₃ CH₂(D-50d) 183.0-186.0 3-046 3,4-Cl₂ CF₃ CH₂CH₂(D-49a) 113.0-116.0 3-047 3,4-Cl₂ CF₃ NHPh 160.0-162.0 3-048 3,4-Cl₂ CF₃ Ph 208.0-210.0 3-049 3,4-Cl₂ CF₃ Ph-2-CH₃-4-Cl 237.0-238.0 3-050 3,4-Cl₂ CF₃ D-35a 238.0-241.0 3-051 3,4-Cl₂ CF₃ D-47a 167.0-169.0 3-052 3,4-Cl₂ CN CH₂CF₃ 162.0-164.0 3-053 3,4-Cl₂ Ph CH₂Pr-c 153.0-154.0 3-054 3,4-Cl₂ Ph CH₂CF₃ 157.0-158.0 3-055 3,4-Cl₂ Ph CH₂Ph 173.0-175.0 3-056 3,5-Cl₂ c-Pr CH₂CF₃ 144.0-145.0 3-057 3,5-Cl₂ CF₃ H 256.0-258.0 3-058 3,5-Cl₂ CF₃ i-Bu 167.0-170.0 3-059 3,5-Cl₂ CF₃ CH₂Cl *1 3-060 3,5-Cl₂ CF₃ CH₂CF₃ 94.0-96.0 3-061 3,5-Cl₂ CF₃ CH₂(T-4) 84.0-87.0 3-062 3,5-Cl₂ CF₃ CH₂OH 254.0-260.0 3-063 3,5-Cl₂ CF₃ CH₂CH(OCH₃)₂ 198.0-200.0 3-064 3,5-Cl₂ CF₃ CH₂CH(OEt)₂ *1 3-065 3,5-Cl₂ CF₃ CH₂CH(CH₃)OC(O)NHEt 127.0-129.0 3-066 3,5-Cl₂ CF₃ CH₂CH(CH₃)OC(O)NH(Ph-4-F) 162.0-165.0 3-067 3,5-Cl₂ CF₃ CH₂CH(OH)CH₂OH *1 3-068 3,5-Cl₂ CF₃ CH₂(E-4a) 123.5-126.0 3-069 3,5-Cl₂ CF₃ CH₂(E-5a) *1 3-070 3,5-Cl₂ CF₃ CH₂(E-10a) 152.0-153.0 3-071 3,5-Cl₂ CF₃ CH₂(E-10b)CH₃ 151.0-153.0 3-072 3,5-Cl₂ CF₃ CH₂(E-32a) *1 3-073 3,5-Cl₂ CF₃ C(CH₃)₂CH₂SCH₃ 91.0-92.0 3-074 3,5-Cl₂ CF₃ C(CH₃)₂CH₂SO₂CH₃ *1 3-075 3,5-Cl₂ CF₃ CH₂(E-18a) 124.0-126.0 3-076 3,5-Cl₂ CF₃ CH₂(E-18c) 253.0-255.0 3-077 3,5-Cl₂ CF₃ CH₂CHO *1 3-078 3,5-Cl₂ CF₃ CH₂CH═NOH *1 3-079 3,5-Cl₂ CF₃ CH₂CH═NOCH₃ *1 3-080 3,5-Cl₂ CF₃ CH₂C(CH₃)═NOCH₃ 71.0-75.0 3-081 3,5-Cl₂ CF₃ CH₂CN 145.0-151.0 3-082 3,5-Cl₂ CF₃ CH₂C(O)OH *1 3-083 3,5-Cl₂ CF₃ CH₂C(O)OCH₃ *1 3-084 3,5-Cl₂ CF₃ CH₂C(O)NH₂ 100.0-107.0 3-085 3,5-Cl₂ CF₃ CH₂C(O)NHCH₂CH₂Cl 161.5-165.0 3-086 3,5-Cl₂ CF₃ CH₂C(O)NHCH₂CF₃ 108.0-114.0 3-087 3,5-Cl₂ CF₃ CH₂C(S)NH₂ *1 3-088 3,5-Cl₂ CF₃ CH₂C(═NOH)NH₂•HCl 140.0-144.5 3-089 3,5-Cl₂ CF₃ CH₂CH═CH₂ *1 3-090 3,5-Cl₂ CF₃ CH₂C(CH₃)═CH₂ 133.0-136.0 3-091 3,5-Cl₂ CF₃ CH₂CCl═CH₂ 121.0-123.0 3-092 3,5-Cl₂ CF₃ CH₂CH═CCl₂ 118.0-120.0 3-093 3,5-Cl₂ CF₃ CH₂CCl═CHCl 153.0-154.0 3-094 3,5-Cl₂ CF₃ CH₂C≡CH 144.0-146.0 3-095 3,5-Cl₂ CF₃ CH₂Ph 174.0-177.0 3-096 3,5-Cl₂ CF₃ CH₂(Ph-4-Br) 203.0-205.0 3-097 3,5-Cl₂ CF₃ CH₂(Ph-4-SCH₃) 182.0-184.0 3-098 3,5-Cl₂ CF₃ CH₂[Ph-4-S(O)CH₃] 170.0-174.0 3-099 3,5-Cl₂ CF₃ CH₂(Ph-4-SO₂CH₃) 214.0-216.0 3-100 3,5-Cl₂ CF₃ CH₂(Ph-2-NO₂) 165.0-167.0 3-101 3,5-Cl₂ CF₃ CH₂(D-1a) 178.5-181.0 3-102 3,5-Cl₂ CF₃ CH₂(D-3a) 201.0-202.0 3-103 3,5-Cl₂ CF₃ CH₂(D-3d)Cl 144.0-146.0 3-104 3,5-Cl₂ CF₃ CH₂(D-10b)Cl 87.0-95.0 3-105 3,5-Cl₂ CF₃ CH₂(D-15a)CH₃ 154.0-155.0 3-106 3,5-Cl₂ CF₃ CH₂(D-16b)Cl 224.0-225.0 3-107 3,5-Cl₂ CF₃ CH₂(D-16c)Cl *1 3-108 3,5-Cl₂ CF₃ CH₂(D-16d) *1 3-109 3,5-Cl₂ CF₃ CH₂(D-17a)CH₃ 59.0-61.0 3-110 3,5-Cl₂ CF₃ CH₂(D-17b)Cl *1 3-111 3,5-Cl₂ CF₃ CH₂(D-21a) 178.0-179.0 3-112 3,5-Cl₂ CF₃ CH₂(D-22a) 156.0-158.0 3-113 3,5-Cl₂ CF₃ CH₂(D-22b)Cl 94.0-96.0 3-114 3,5-Cl₂ CF₃ CH₂(D-22b)CH₃ *1 3-115 3,5-Cl₂ CF₃ CH₂(D-23a) 191.0-193.0 3-116 3,5-Cl₂ CF₃ CH₂(D-23b)Cl 165.0-167.0 3-117 3,5-Cl₂ CF₃ CH₂(D-24b) 218.0-220.0 3-118 3,5-Cl₂ CF₃ CH₂(D-24c) *1 3-119 3,5-Cl₂ CF₃ CH₂(D-25a)CH₃ *1 3-120 3,5-Cl₂ CF₃ CH₂(D-27a)CH₃ *1 3-121 3,5-Cl₂ CF₃ CH₂(D-29b)CH₃ *1 3-122 3,5-Cl₂ CF₃ CH₂(D-34a) *1 3-123 3,5-Cl₂ CF₃ CH₂(D-35a) 157.5-161.0 3-124 3,5-Cl₂ CF₃ CH₂(D-38a) 224.5-226.0 3-125 3,5-Cl₂ CF₃ CH₂(D-47a) 150.0-151.0 3-126 3,5-Cl₂ CF₃ CH₂(D-47c)Cl 124.0-126.0 3-127 3,5-Cl₂ CF₃ CH₂(D-47e)CH₃ *2 3-128 3,5-Cl₂ CF₃ CH₂(D-47i) 121.0-124.0 3-129 3,5-Cl₂ CF₃ CH₂(D-48e)Cl 159.5-163.0 3-130 3,5-Cl₂ CF₃ CH₂(D-50d) 250.0-255.0 3-131 3,5-Cl₂ CF₃ CH₂(D-53b)CH₃ *1 3-132 3,5-Cl₂ CF₃ CH(CH₃)Ph 137.5-141.0 3-133 3,5-Cl₂ CF₃ C(O)(D-47a) *1 3-134 3,5-Cl₂ CF₃ OCH₃ *1 3-135 3,5-Cl₂ CF₃ NH(D-47a) *1 3-136 3,5-Cl₂ CF₃ NH(D-50a) 202.0-204.0 3-137 3,5-Cl₂ CF₃ NH(D-50b)CF₃ 146.0-149.0 3-138 3,5-Cl₂ CF₃ NH(D-54b)Cl 124.0-130.0 3-139 3,5-Cl₂ CF₃ N(CH₃)Ph 174.0-178.0 3-140 3,5-Cl₂ CF₃ D-21a 268.0-273.0 3-141 3-CH₃-4-F CF₃ CH₂CF₃ 151.0-152.0 3-142 3-Cl-5-CH₃ CF₃ CH₂CF₃ 74.0-76.0 3-143 3-Cl-5-CH₃ CF₃ CH₂(D-47a) *1 3-144 3-Cl-4-OCH₃ CF₃ CH₂CF₃ 135.0-138.0 3-145 3-CF₃-5-OCH₃ CF₃ CH₂CF₃ 161.0-162.0 3-146 3-OCH₂O-4 CF₃ CH₂CF₃ 149.0-151.0 3-147 2-F-3-CH₃-5-Cl CF₃ CH₂CF₃ *1 3-148 3,5-Cl₂ CF₃ CH₂(D-34b)CH₃ 143.0-144.5 3-149 3,5-Cl₂ CF₃ NH₂ 170.0-172.0 3-150 3,5-Cl₂ CF₃ Ph-4-F 166.0-168.0 3-151 3,5-Cl₂ CF₃ E-4a 210.0-213.0

TABLE 10

No. (X)_(m) R³ R² R¹ m.p. (° C.) 4-001 3,4-Cl₂ CF₃ —CH₂CH₂CH(CH₃)CH₂CH₂— 132.0-134.0 4-002 3,4-Cl₂ CF₃ —CH₂CH₂CH₂CH₂CH₂CH₂— 160.0-163.0 4-003 3,5-Cl₂ CF₃ CH₂OCH₃ CH₂(D-47a) *1 4-004 3,5-Cl₂ CF₃ CH₂OEt CH₂(D-47a) *1 4-005 3,5-Cl₂ CF₃ CH₂SO₂CH₃ CH₂(D-47a) *1 4-006 3,5-Cl₂ CF₃ CH₂CH═CH₂ CH₂(D-47a) *1 4-007 3,5-Cl₂ CF₃ CH(CH═CH₂)CH₂CH═CH₂ CH₂(D-47a) *1 4-008 3,5-Cl₂ CF₃ CH₂Ph CH₂(D-47a) *1 4-009 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂(D-47a) *1 4-010 3,5-Cl₂ CF₃ Et CH₂(D-48e)Cl *1 4-011 3,5-Cl₂ CF₃ CH₃ OCH₃ *1

TABLE 11

No. (X)_(m) R³ (Y)_(n) R¹ m.p. (C. °) 5-001 3-Cl CF₃ 2-CH₃ CH₂(D-47a) *1 5-002 3-Br CF₃ 2-CH₃ CH₂CF₃ 158.5-161.0 5-003 3-Br CF₃ 2-CH₃ CH₂(D-47a) *1 5-004 3-I CF₃ 2-CH₃ CH₂CF₃ 168.0-172.5 5-005 3-I CF₃ 2-CH₃ CH₂(D-47a) 135.5-138.0 5-006 4-I CF₃ 2-CH₃ CH₂CF₃ 134.0-135.0 5-007 4-I CF₃ 2-CH₃ CH₂(D-47a) *1 5-008 3-CF₃ CF₃ 2-CH₃ CH₂CF₃ 135.5-137.5 5-009 3-CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-010 3-(T-4) CF₃ 2-CH₃ CH₂CF₃ *2 5-011 3-(T-4) CF₃ 2-CH₃ CH₂(D-47a) *2 5-012 3-OCF₃ CF₃ 2-CH₃ CH₂CF₃ *2 5-013 3-OCF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-014 3-OCF₂Br CF₃ 2-CH₃ CH₂CF₃ *1 5-015 3-OCF₂Br CF₃ 2-CH₃ CH₂(D-47a) *2 5-016 3-OCF₂CHFOCF₂CF₂CF₃ CF₃ 2-CH₃ CH₂CF₃ *1 5-017 3-OCF₂CHFOCF₂CF₂CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-018 3-OCH₂(Ph-2-Cl) CF₃ 2-CH₃ CH₂(D-47a) *1 5-019 3-O[(D-47f)-3-Cl-5-CF₃] CF₃ 2-CH₃ CH₂CF₃ *1 5-020 3-O[(D-47f)-3-Cl-5-CF₃] CF₃ 2-CH₃ CH₂(D-47a) *1 5-021 3-SEt CF₃ 2-CH₃ CH₂(D-47a) *1 5-022 3-SCF₃ CF₃ 2-CH₃ CH₂CF₃ *1 5-023 3-SCF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-024 3-N(CH₃)C(O)CF₃ CF₃ 2-CH₃ CH₂CF₃ *1 5-025 3-N(CH₃)C(O)CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-026 3-N(CH₃)SO₂CF₃ CF₃ 2-CH₃ CH₂CF₃ *1 5-027 3-N(CH₃)SO₂CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-028 3-Ph CF₃ 2-CH₃ CH₂(D-47a) *1 5-029 3,5-F₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-030 3,5-Cl₂ CH₃ 2-CH₃ CH₂CF₃ *1 5-031 3,5-Cl₂ i-Pr 2-CH₃ CH₂CF₃ *1 5-032 3,5-Cl₂ c-Pr 2-CH₃ CH₂CF₃ 157.0-158.0 5-033 3,5-Cl₂ c-Pr 2-CH₃ CH₂(D-47a) *1 5-034 3,5-Cl₂ CH₂Cl 2-CH₃ CH₂CF₃ 117.0-119.0 5-035 3,5-Cl₂ CH₂Cl 2-CH₃ CH₂(D-47a) *1 5-036 3,5-Cl₂ CHF₂ 2-CH₃ CH₂CF₃ 94.0-97.5 5-037 3,5-Cl₂ CHF₂ 2-CH₃ CH₂(D-47a) *1 5-038 3,5-Cl₂ CF₃ 2-F CH₂CF₃ *1 5-039 3,5-Cl₂ CF₃ 2-F CH₂Ph 172.0-176.0 5-040 3,5-Cl₂ CF₃ 2-F CH₂(D-22a) *1 5-041 3,5-Cl₂ CF₃ 2-F CH₂(D-47a) 126.0-129.0 5-042 3,5-Cl₂ CF₃ 3-F CH₂CF₃ *1 5-043 3,5-Cl₂ CF₃ 3-F CH₂Ph 178.0-181.0 5-044 3,5-Cl₂ CF₃ 3-F CH₂(D-47a) 125.0-127.0 5-045 3,5-Cl₂ CF₃ 2-Cl CH₂Pr-c 132.0-134.0 5-046 3,5-Cl₂ CF₃ 2-Cl CH₂CF₃ 124.0-125.0 5-047 3,5-Cl₂ CF₃ 2-Cl CH₂Ph 57.0-58.0 5-048 3,5-Cl₂ CF₃ 2-Cl CH₂(Ph-4-NO₂) *1 5-049 3,5-Cl₂ CF₃ 2-Cl CH₂(D-21a) *1 5-050 3,5-Cl₂ CF₃ 2-Cl CH₂(D-22a) *1 5-051 3,5-Cl₂ CF₃ 2-Cl CH₂(D-22b)Ol *2 5-052 3,5-Cl₂ CF₃ 2-Cl CH₂(D-28a) *1 5-053 3,5-Cl₂ CF₃ 2-Cl CH₂(D-47a) *1 5-054 3,5-Cl₂ CF₃ 3-Cl CH₂CF₃ 149.0-150.0 5-055 3,5-Cl₂ CF₃ 3-Cl CH₂Ph 119.0-121.0 5-056 3,5-Cl₂ CF₃ 3-Cl CH₂(D-47a) *1 5-057 3,5-Cl₂ CF₃ 2-Br CH₂CF₃ 145.0-147.0 5-058 3,5-Cl₂ CF₃ 2-Br CH₂(D-47a) *1 5-059 3,5-Cl₂ CF₃ 2-I CH₂CF₃ 128.0-130.0 5-060 3,5-Cl₂ CF₃ 2-I CH₂CH₂OEt *1 5-061 3,5-Cl₂ CF₃ 2-I CH₂CH(OCH₃)₂ *1 5-062 3,5-Cl₂ CF₃ 2-I CH₂C(O)NHCH₃ *1 5-063 3,5-Cl₂ CF₃ 2-I CH₂C(O)NHCH₂CH₂Cl 68.0-70.0 5-064 3,5-Cl₂ CF₃ 2-I CH₂CH═CH₂ 97.0-100.0 5-065 3,5-Cl₂ CF₃ 2-I CH₂(D-47a) *1 5-066 3,5-Cl₂ CF₃ 2-CH₃ H 162.0-164.0 5-067 3,5-Cl₂ CF₃ 2-CH₃ Et 129.5-133.0 5-068 3,5-Cl₂ CF₃ 2-CH₃ c-Pr 84.0-86.0 5-069 3,5-Cl₂ CF₃ 2-CH₃ i-Bu 138.0-140.0 5-070 3,5-Cl₂ CF₃ 2-CH₃ CH₂Pr-c *1 5-071 3,5-Cl₂ CF₃ 2-CH₃ c-Bu 139.0-141.0 5-072 3,5-Cl₂ CF₃ 2-CH₃ CH₂Bu-c *1 5-073 3,5-Cl₂ CF₃ 2-CH₃ c-Pen 155.0-158.0 5-074 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂Cl 161.5-164.5 5-075 3,5-Cl₂ CF₃ 2-CH₃ CH₂CF₃ 155.5-157.0 5-075(+) 99% e.e. [α]_(D) ^(23.0) + 74.38° (EtOH, c = 0.621) *1 5-075(−) 99% e.e. [α]_(D) ^(22.8) − 70.98° (EtOH, c = 0.648) *1 5-076 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₃ 115.0-117.0 5-077 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OEt *1 5-078 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₂CH₂Cl 140.0-142.0 5-079 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OC(O)CH₃ *2 5-080 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OC(O)NHEt *2 5-081 3,5-Cl₂ CF₃ 2-CH₃ CH₂OH(CH₃)OH 67.0-70.0 5-082 3,5-Cl₂ CF₃ 2-CH₃ CH₂OH(CH₃)OCH₃ 179.0-181.0 5-083 3,5-Cl₂ CF₃ 2-CH₃ CH₂OH(OCH₃)₂ *1 5-084 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(OEt)₂ *2 5-085 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OC(O)NHEt *1 5-086 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-4a) *1 5-087 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-5a) *2 5-088 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-10a) 158.5-160.5 5-089 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-10b)CH₃ 153.0-154.0 5-090 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-32a) *1 5-091 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SCH₃ 121.0-127.0 5-092 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂S(O)CH₃ *1 5-093 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SEt 106.0-109.0 5-094 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SO₂Et *1 5-095 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SCH₂Ph *1 5-096 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SO₂CH₂Ph *1 5-097 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SCH₂(D-1a) *1 5-098 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SO₂CH₂(D-1a) *1 5-099 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)SCH₃ *1 5-100 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)S(O)CH₃ *1 5-101 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)SO₂CH₃ *1 5-102 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂SCH₃ *1 5-103 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂SO₂CH₃ *1 5-104 3,5-Cl₂ CF₃ 2-CH₃ C(CH₃)₂CH₂SCH₃ *1 5-105 3,5-Cl₂ CF₃ 2-CH₃ C(CH₃)₂CH₂SO₂CH₃ 167.0-169.0 5-106 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-18a) 204.0-206.0 5-107 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-18c) 249.0-251.0 5-108 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-43a) 199.0-201.0 5-109 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHC(O)CF₃ 81.0-84.0 5-110 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHC(O)CH₂CF₃ 143.0-146.0 5-111 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)CH₃ 155.0-160.0 5-112 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOH *1 5-113 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₃ *2 5-114 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂Pr-c *1 5-115 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂(Ph-4-Cl) *2 5-116 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂CH₂-TMS *1 5-117 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(CH₃)═NOCH₃ 101.0-105.0 5-118 3,5-Cl₂ CF₃ 2-CH₃ CH₂(M-5a)CH₃ *1 5-119 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN 186.5-189.0 5-120 3,5-Cl₂ CF₃ 2-CH₃ CH(OCH₂CF₃)CN *1 5-121 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)CN 165.5-167.0 5-122 3,5-Cl₂ CF₃ 2-CH₃ CH(D-1a)CN *1 5-123 3,5-Cl₂ CF₃ 2-CH₃ CH(D-3a)CN *1 5-124 3,5-Cl₂ CF₃ 2-CH₃ CH(D-14a)CN 192.0-194.5 5-125 3,5-Cl₂ CF₃ 2-CH₃ CH(D-38a)CN 185.0-189.5 5-126 3,5-Cl₂ CF₃ 2-CH₃ CH(D-47a)CN *1 5-127 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OH 195.0-197.0 5-128 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OCH₃ *2 5-129 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OCH₂CF₃ 157.0-158.0 5-130 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)OCH₃(D) *1 5-131 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)OEt(L) *1 5-132 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)OCH₂CF₃ *1 5-133 3,5-Cl₂ CF₃ 2-CH₃ CH(OH)C(O)OCH₃ *1 5-134 3,5-Cl₂ CF₃ 2-CH₃ CH(OCH₃)C(O)OCH₃ *1 5-135 3,5-Cl₂ CF₃ 2-CH₃ CH(D-14a)C(O)OCH₃ 93.5-97.0 5-136 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂C(O)OEt *1 5-137 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NH₂ 87.0-91.0 5-138 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₃ *1 5-139 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)₂ *1 5-140 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHEt 137.5-141.0 5-141 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPr-n *1 5-142 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPr-i 152.0-155.0 5-143 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-i *1 5-144 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-c 174.0-177.0 5-145 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-t *1 5-146 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂Bu-t *1 5-147 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂F *1 5-148 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂Cl 109.0-112.0 5-149 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)CH₂CH₂Cl *2 5-150 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂Br *1 5-151 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CF₃ 173.5-175.5 5-151(+) 99% e.e. [α]_(D) ^(23.1) + 61.96° (EtOH, c = 1.098) *1 5-151(−) 99% e.e. [α]_(D) ^(23.1) − 58.95° (EtOH, c = 1.153) *1 5-152 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂CH₂Cl *1 5-153 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂(T-4) *1 5-154 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂OH *1 5-155 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)CH₂CH₂OH *1 5-156 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂OCH₃ 146.0-149.0 5-157 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂OEt *1 5-158 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂SCH₃ 138.0-143.0 5-159 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂SO₂CH₃ *1 5-160 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH═CH₂ 76.0-79.0 5-161 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)CH₂CH═CH₂ *1 5-162 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₂OH═CH₂)₂ *1 5-163 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CCl═CH₂ *1 5-164 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH═CCl₂ 188.0-192.0 5-165 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂C≡CH *1 5-166 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂Ph 187.0-191.0 5-167 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂(D-22a) *1 5-168 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂(D-47a) *1 5-169 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPh 181.0-183.0 5-170 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)(T-37) 118.0-121.0 5-171 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)(T-40) *1 5-172 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHNHCH₂CF₃ 118.0-120.0 5-173 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHN(CH₃)Ph *1 5-174 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH₂Cl 146.0-149.0 5-175 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)C(O)NHCH₃(R) 118.0-121.0 5-176 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)C(O)NHCH₃(S) *1 5-177 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂C(O)NHCH₂CH₂Cl 153.0-157.0 5-178 3,5-Cl₂ CF₃ 2-CH₃ CH₂(T-22) *1 5-179 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(S)NH₂ *1 5-180 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)O(S)NH₂ *1 5-181 3,5-Cl₂ CF₃ 2-CH₃ CH₂Si(CH₃)₃ *1 5-182 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═CH₂ *1 5-183 3,5-Cl₂ CF₃ 2-CH₃ CH₂CCl═CH₂ *1 5-184 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═CCl₂ *1 5-185 3,5-Cl₂ CF₃ 2-CH₃ CH₂CCl═CHCl *1 5-186 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CH *1 5-187 3,5-Cl₂ CF₃ 2-CH₃ CH₂Ph 142.0-144.5 5-188 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)Ph 121.5-123.5 5-189 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)Ph(R) *1 5-189(+) 99% d.e. [α]_(D) ^(22.9) + 59.13° (EtOH, c = 0.262) *1 5-189(−) 99% d.e. [α]_(D) ^(23.0) − 86.72° (EtOH, c = 0.250) *1 5-190 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)Ph(S) *1 5-190(+) 99% d.e. [α]_(D) ^(23.0) + 89.06° (EtOH, c = 0.466) *1 5-190(−) 99% d.e. [α]_(D) ^(23.0) − 117.66° (EtOH, c = 0.322) *1 5-191 3,5-Cl₂ CF₃ 2-CH₃ CH(Et)Ph *1 5-192 3,5-Cl₂ CF₃ 2-CH₃ C(CH₃)₂Ph 91.0-93.5 5-193 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)Ph 175.5-180.0 5-194 3,5-Cl₂ CF₃ 2-CH₃ CH(OEt)Ph *2 5-195 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-2-F) 151.0-153.0 5-196 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3-F) 134.0-136.0 5-197 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-4-F) 153.0-155.0 5-198 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-2-Cl) 147.0-149.0 5-199 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3-Cl) 160.0-162.0 5-200 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-4-Cl) 164.0-166.0 5-201 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3-NO₂) 198.0-200.0 5-202 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-4-NO₂) 204.0-206.0 5-203 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-2,5-F₂) 153.0-155.0 5-204 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3,5-F₂) 146.0-149.0 5-205 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-1a) *1 5-206 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-3a) 147.0-148.5 5-207 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-3d)Cl *1 5-208 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-8b)CH₃ *1 5-209 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-10b)Cl *1 5-210 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-15a)CH₃ 147.0-148.0 5-211 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-16b)Cl 237.0-238.0 5-212 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-16c)Cl *1 5-213 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-16d) *1 5-214 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-17a)CH₃ 76.0-77.0 5-215 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-17b)Cl 157.0-158.0 5-216 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-21a) *1 5-217 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)(D-21a) *1 5-218 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-21b)CF₃ *1 5-219 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a) 135.0-136.5 5-219(+) 97% e.e. [α]_(D) ^(22.6) + 56.54° (EtOH, c = 0.384) *1 5-219(−) 99% e.e. [α]_(D) ^(22.4) − 58.65° (EtOH, c = 0.393) *1 5-220 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)Cl *1 5-221 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)CH₃ *1 5-222 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-23a) *1 5-223 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-23b)Cl *1 5-224 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-25a)CH₃ *1 5-225 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-27a)CH₃ *1 5-226 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-28a) *1 5-227 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-29b)CH₃ *1 5-228 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-30a) 120.0-123.5 5-229 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-31a) 122.0-125.0 5-230 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-34a) *1 5-231 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-34b)CH₃ *1 5-232 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-35a) *1 5-233 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-38a) *1 5-234 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47a) 131.0-135.5 5-235 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-47a) *1 5-236 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47c)Cl 164.0-166.0 5-237 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47c)NO₂ 129.0-131.0 5-238 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47e)Cl *1 5-239 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47i) *1 5-240 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-48a) *1 5-241 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-48e)Cl 200.5-202.0 5-242 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-49a) *1 5-243 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-50a) *1 5-244 3,5-Cl₂ CF₃ 2-CH₃ CH₂[(D-50d)-4,6-(OCH₃)₂] 58.0-65.0 5-245 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-51a) *1 5-246 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-53a) *1 5-247 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-53b)CH₃ *1 5-248 3,5-Cl₂ CF₃ 2-CH₃ NH₂ 87.0-89.0 5-249 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)₂ 79.0-84.0 5-250 3,5-Cl₂ CF₃ 2-CH₃ NHBu-t 71.0-76.0 5-251 3,5-Cl₂ CF₃ 2-CH₃ NHCH₂CF₃ 158.0-159.0 5-252 3,5-Cl₂ CF₃ 2-CH₃ NHCH₂CH₂OH 61.0-70.0 5-253 3,5-Cl₂ CF₃ 2-CH₃ T-34a 59.0-63.0 5-254 3,5-Cl₂ CF₃ 2-CH₃ T-40 95.0-105.0 5-255 3,5-Cl₂ CF₃ 2-CH₃ T-42 155.0-157.0 5-256 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₃ 117.0-118.0 5-257 3,5-Cl₂ CF₃ 2-CH₃ N(Ph)C(O)CH₃ 89.0-99.0 5-258 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)Pr-n 109.0-111.0 5-259 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₂CH₂Cl 109.0-110.0 5-260 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₂CN 121.0-125.0 5-261 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)OCH₃ 86.0-93.0 5-262 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)C(O)OCH₃ 131.0-132.0 5-263 3,5-Cl₂ CF₃ 2-CH₃ N(Ph)C(O)OCH₃ 98.0-106.0 5-264 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)OEt 75.0-84.0 5-265 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)OBu-t *1 5-266 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)OCH₂Ph 155.0-156.0 5-267 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)NHPh 212.0-214.0 5-268 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)Ph 213.0-214.0 5-269 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)(D-1a) 230.0-232.0 5-270 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)(D-47a) 116.0-117.0 5-271 3,5-Cl₂ CF₃ 2-CH₃ NHC(S)NHCH₃ 143.0-145.0 5-272 3,5-Cl₂ CF₃ 2-CH₃ NHC(S)N(CH₃)₂ 179.0-182.0 5-273 3,5-Cl₂ CF₃ 2-CH₃ NHPh 88.0-96.0 5-274 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)Ph 158.0-160.0 5-275 3,5-Cl₂ CF₃ 2-CH₃ N(CH₂CH═CH₂)Ph 78.0-86.0 5-276 3,5-Cl₂ CF₃ 2-CH₃ N(CH₂Ph)Ph 58.0-60.0 5-277 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-2-Cl) *1 5-278 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-3-Cl) *1 5-279 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-4-Cl) *1 5-280 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-4-CF₃) *1 5-281 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-2-NO₂) 89.0-95.0 5-282 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-3-NO₂) 104.0-109.0 5-283 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-4-NO₂) 120.0-126.0 5-284 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)(D-21a) 181.0-185.0 5-285 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47a) 213.0-217.0 5-286 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)(D-47a) 202.0-203.0 5-287 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47b)Cl 102.0-103.0 5-288 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47d)Cl 91.0-92.0 5-289 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47e)Cl 89.0-90.0 5-290 3,5-Cl₂ CF₃ 2-CH₃ NH[(D-47f)-3-Cl-5-CF₃] 137.0-140.0 5-291 3,5-Cl₂ CF₃ 2-CH₃ NH(D-50a) 209.0-211.0 5-292 3,5-Cl₂ CF₃ 2-CH₃ NH(D-50b)CF₃ 95.0-100.0 5-293 3,5-Cl₂ CF₃ 2-CH₃ NH[(D-50d)-4,6-(OCH₃)₂] 91.0-98.0 5-294 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)(D-50a) 194.0-196.0 5-295 3,5-Cl₂ CF₃ 2-CH₃ N(Et)(D-50a) 60.0-67.0 5-296 3,5-Cl₂ CF₃ 2-CH₃ NH(D-51b)SCH₃ *1 5-297 3,5-Cl₂ CF₃ 2-CH₃ NH(D-51b)S(O)CH₃ 156.0-162.0 5-298 3,5-Cl₂ CF₃ 2-CH₃ NH(D-51b)SO₂CH₃ 147.0-151.0 5-299 3,5-Cl₂ CF₃ 2-CH₃ NH(D-51c)Cl *1 5-300 3,5-Cl₂ CF₃ 2-CH₃ NH(D-53a) 111.0-112.0 5-301 3,5-Cl₂ CF₃ 2-CH₃ NH(D-54b)Cl *1 5-302 3,5-Cl₂ CF₃ 2-CH₃ N═C(CH₃)Ph 134.0-135.0 5-303 3,5-Cl₂ CF₃ 2-CH₃ N═CH(D-47a) *1 5-304 3,5-Cl₂ CF₃ 2-CH₃ T-47 146.0-148.0 5-305 3,5-Cl₂ CF₃ 2-CH₃ D-8a 127.5-129.0 5-306 3,5-Cl₂ CF₃ 2-CH₃ (D-13b)CH₃ 271.0-275.0 5-307 3,5-Cl₂ CF₃ 2-CH₃ D-21a 281.0-284.0 5-308 3,5-Cl₂ CF₃ 2-CH₃ D-48a 188.0-190.0 5-309 3,5-Cl₂ CF₃ 2-CH₃ D-50a 98.0-100.0 5-310 3,5-Cl₂ CF₃ 2-CH₃ D-51a 90.0-91.0 5-311 3,5-Cl₂ CF₃ 3-CH₃ CH₂CF₃ *1 5-312 3,5-Cl₂ CF₃ 2-Et CH₂CF₃ *1 5-313 3,5-Cl₂ CF₃ 2-Et CH₂(D-47a) *1 5-314 3,5-Cl₂ CF₃ 2-CF₃ CH₂CF₃ 70.0-72.0 5-315 3,5-Cl₂ CF₃ 2-CF₃ CH₂(D-47a) 69.0-70.0 5-316 3,5-Cl₂ CF₃ 2-CH₂OH CH₂CF₃ *1 5-317 3,5-Cl₂ CF₃ 2-OCH₃ CH₂CF₃ *1 5-318 3,5-Cl₂ CF₃ 2-OCH₃ CH₂Ph *1 5-319 3,5-Cl₂ CF₃ 2-OCH₃ CH₂(D-47a) 173.5-176.0 5-320 3,5-Cl₂ CF₃ 2-OCF₃ CH₂CF₃ *2 5-321 3,5-Cl₂ CF₃ 2-OCF₃ CH₂(D-47a) 145.0-148.5 5-322 3,5-Cl₂ CF₃ 2-SCH₃ CH₂CF₃ *2 5-323 3,5-Cl₂ CF₃ 2-SCH₃ CH₂(D-47a) *2 5-324 3,5-Cl₂ CF₃ 2-S(O)CH₃ CH₂CF₃ *2 5-325 3,5-Cl₂ CF₃ 2-S(O)CH₃ CH₂(D-47a) *1 5-326 3,5-Cl₂ CF₃ 2-SO₂CH₃ CH₂CF₃ *1 5-327 3,5-Cl₂ CF₃ 2-SO₂CH₃ CH₂(D-47a) 120.0-121.0 5-328 3,5-Cl₂ CF₃ 2-S(O)CH₂Cl CH₂CF₃ *2 5-329 3,5-Cl₂ CF₃ 2-NH₂ CH₂CF₃ 78.0-79.0 5-330 3,5-Cl₂ CF₃ 2-NH₂ CH₂(D-47a) *2 5-331 3,5-Cl₂ CF₃ 2-NHCH₃ CH₂CF₃ 156.0-158.0 5-332 3,5-Cl₂ CF₃ 2-NHCH₃ CH₂(D-47a) *1 5-333 3,5-Cl₂ CF₃ 2-NHC(O)CH₃ CH₂CF₃ *2 5-334 3,5-Cl₂ CF₃ 2-N(CH₃)2 CH₂CF₃ *2 5-335 3,5-Cl₂ CF₃ 2-N(CH₃)2 CH₂(D-47a) *1 5-336 3,5-Cl₂ CF₃ 2-N(CH₃)CHO CH₂(D-47a) *1 5-337 3,5-Cl₂ CF₃ 2-N(CH₃)C(O)CH₃ CH₂(D-47a) *1 5-338 3,5-Cl₂ CF₃ 2-NO₂ CH₂CF₃ 180.0-181.0 5-339 3,5-Cl₂ CF₃ 2-NO₂ CH₂(D-47a) *2 5-340 3,5-Cl₂ CF₃ 2-CN CH₂CF₃ *1 5-341 3,5-Cl₂ CF₃ 2-CN CH₂(D-47a) *1 5-342 3,5-Cl₂ CF₃ 2-C≡C-TMS CH₂CF₃ *1 5-343 3,5-Cl₂ CF₃ 2-Ph CH₂CF₃ *1 5-344 3,5-Cl₂ CF₃ 2-Ph CH₂(D-47a) 194.0-198.0 5-345 3,5-Cl₂ CF₃ 2-(D-38a) CH₂(D-47a) *2 5-346 3,5-Cl₂ CF₃ 2,3-F₂ CH₂CF₃ *1 5-347 3,5-Cl₂ CF₃ 2,3-F₂ CH₂Ph *1 5-348 3,5-Cl₂ CF₃ 2,3-F₂ CH₂(D-47a) *1 5-349 3,5-Cl₂ CF₃ 2,6-F₂ CH₂CF₃ 140.0-141.0 5-350 3,5-Cl₂ CF₃ 2,6-Cl₂ CH₂(D-47a) 131.0-132.0 5-351 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ CH₂CF₃ 125.0-129.0 5-352 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ CH₂(D-47a) *1 5-353 3,5-Cl₂ CF₂CF₃ 2-Cl CH₂(D-22a) *1 5-354 3,5-Cl₂ CF₂CF₃ 2-Cl CH₂(D-47a) *1 5-355 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂CF₃ *1 5-356 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂CH₂OEt *1 5-357 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂CH(OCH₃)₂ *1 5-358 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂CH═CH₂ *1 5-359 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂(D-22a) *1 5-360 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂(D-47a) *1 5-361 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂CF₃ *1 5-362 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂(D-47a) *1 5-363 3,5-Cl₂ CF₂CF₃ 2-CH₃ C(O)(D-47a) *1 5-364 3,5-Cl₂ CH₂OCH₂CF₃ 2-CH₃ CH₂CF₃ *1 5-365 3,5-Cl₂ CH₂OCH₂CF₃ 2-CH₃ CH₂(D-47a) *1 5-366 3,5-Cl₂ CF₂SCH₃ 2-CH₃ CH₂CF₃ *2 5-367 3,5-Cl₂ CF₂SCH₃ 2-CH₃ CH₂(D-47a) 51.0-52.0 5-368 3,5-Cl₂ CH₂-TMS 2-CH₃ CH₂CF₃ *1 5-369 3,5-Cl₂ CH₂-TMS 2-CH₃ CH₂(D-47a) *1 5-370 3,5-Cl₂ TMS 2-CH₃ CH₂CF₃ *1 5-371 3,5-Cl₂ TMS 2-CH₃ CH₂(D-47a) *1 5-372 3,5-Cl₂ D-47a 2-CH₃ CH₂CF₃ *1 5-373 3,5-Cl₂ D-47a 2-CH₃ CH₂(D-47a) *1 5-374 3-Cl-5-Br CF₃ 2-CH₃ CH₂CF₃ *1 5-375 3-Cl-5-Br CF₃ 2-CH₃ CH₂(D-47a) *1 5-376 3,5-Br₂ CF₃ 2-Cl CH₂(D-22a) 63.0-64.0 5-377 3,5-Br₂ CF₃ 2-Cl CH₂(D-47a) *2 5-378 3,5-Br₂ CF₃ 2-CH₃ CH₂CF₃ *1 5-379 3,5-Br₂ CF₃ 2-CH₃ CH₂CH₂OCH₃ *2 5-380 3,5-Br₂ CF₃ 2-CH₃ CH₂CH₂OEt *2 5-381 3,5-Br₂ CF₃ 2-CH₃ CH₂OH(OCH₃)₂ *2 5-382 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)OCH₃ *2 5-383 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂Cl 69.0-70.0 5-384 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CF₃ 173.0-175.0 5-385 3,5-Br₂ CF₃ 2-CH₃ CH₂OH═CH₂ *2 5-386 3,5-Br₂ CF₃ 2-CH₃ CH₂(D-22a) *1 5-387 3,5-Br₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-388 3-Cl-5-CH₃ CF₃ 2-CH₃ CH₂(D-47a) *2 5-389 3,5-(CF₃)₂ CF₃ 2-CH₃ CH₂CF₃ *1 5-390 3,5-(CF₃)₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-391 3-F-5-SCH₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-392 3-Cl-5-SCH₃ CF₃ 2-SOH3 CH₂(D-47a) *2 5-393 3-CF₃-5-OCH₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-394 3,5-(SCH₃)₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-395 3-CF₃-5-CN CF₃ 2-CH₃ CH₂CF₃ 72.0-73.0 5-396 3-CF₃-5-CN CF₃ 2-CH₃ CH₂(D-47a) 63.0-64.0 5-397 3,4,5-Cl₃ CF₃ 2-CH₃ CH₂CF₃ 194.0-197.0 5-398 3,4,5-Cl₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-399 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂CF₃ *1 5-400 3,5-Cl₂ CF₃ 2-CH₃ OH(CF₃)OH *1 5-401 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)OCH₃ *1 5-402 3,5-Cl₂ CF₃ 2-CH₃ E-5b 197.0-199.0 5-403 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂(T-33) *1 5-404 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂(T-39) *1 5-405 3,5-Cl₂ CF₃ 2-CH₃ (E-9b)CH₂CF₃ *2 5-406 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-17a)H *1 5-407 3,5-Cl₂ CF₃ 2-CH₃ CH[C(O)OCH₃]₂ *2 5-408 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHOEt 141.0-145.0 5-409 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHOCH₂OH═CH₂ *1 5-410 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHEt *1 5-411 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHPr-i 172.0-174.0 5-412 3,5-Cl₂ CF₃ 2-CH₃ OH(CH₃)C(O)NHCH₂CF₃ 161.0-163.0 5-413 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH═CH₂ 175.0-178.0 5-414 3,5-Cl₂ CF₃ 2-CH₃ T-48 *2 5-415 3,5-Cl₂ CF₃ 2-CH₃ T-49 *2 5-416 3,5-Cl₂ CF₃ 2-CH₃ CH[C(O)NHCH₃]₂ 146.0-149.0 5-417 3,5-Cl₂ CF₃ 2-CH₃ CH(OCH₃)Ph *1 5-418 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-1a) 142.0-144.0 5-419 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-6a)CH₃ 155.0-157.0 5-420 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)(D-6a)H *1 5-421 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-11a) *1 5-422 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)(D-14a) 114.0-118.0 5-423 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-21a) *2 5-424 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)(D-24a) *1 5-425 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-26a)CH₃ *1 5-426 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-38a) *1 5-427 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)(D-38a) *1 5-428 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CF₃ *1 5-429 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂CF₃ 81.5-83.0 5-430 3,5-Cl₂ CF₃ 2-CH₃ C(S)NHCH₂CF₃ 137.5-140.0 5-431 3,5-Cl₂ CF₃ 2-CH₃ C(D-49a)═C(CN)₂ 122.0-124.0 5-432 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)NHCH₂CH₂Cl 105.0-108.0 5-433 3,5-Cl₂ CF₃ 2-CH₃ N(CH₂C≡CH)Ph 76.0-84.0 5-434 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-CN *1 5-435 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)OH 248.0-251.0 5-436 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)OEt 230.0-232.0 5-437 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)NHCH₂CH₂Cl 188.0-195.0 5-438 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)NHCH₂CF₃ 110.0-120.0 5-439 3,5-Cl₂ CF₃ 2-CH₃ (D-8b)CH₃ 163.0-165.0 5-440 3,5-Cl₂ CF₃ 2-CH₃ (D-15a)CH₃ 96.0-110.0 5-441 3,5-Cl₂ CF₃ 2-CH₃ (D-17a)CH₃ 95.0-101.0 5-442 3,5-Cl₂ CF₃ 2-CH₃ (D-17b)Cl 100.0-108.0 5-443 3,5-Cl₂ CF₃ 2-CH₃ (D-21b)CH₃ 110.0-114.0 5-444 3,5-Cl₂ CF₃ 2-CH₃ (D-21c)Cl 288.0-292.0 5-445 3,5-Cl₂ CF₃ 2-CH₃ (D-21c)CH₃ 271.0-273.0 5-446 3,5-Cl₂ CF₃ 2-CH₃ D-35a 117.0-126.0 5-447 3,5-Cl₂ CF₃ 2-CH₃ (D-35b)CH₃ 227.0-230.0 5-448 3,5-Cl₂ CF₃ 2-CH₃ (D-39c)SCH₃ 188.0-190.0 5-449 3,5-Cl₂ CF₃ 2-CH₃ (D-42a)H 109.0-112.0 5-450 3,5-Cl₂ CH(OEt)2 2-CH₃ CH₂(D-47a) *1 5-451 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)OH 102.0-106.0 5-452 3-CF₃-5-NO₂ CF₃ 2-CH₃ CH₂CF₃ *1 5-453 3-CF₃-5-NO₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-454 3,5-Cl₂-4-NH₂ CF₃ 2-CH₃ CH₂CF₃ 153.0-154.0 5-455 3,5-Cl₂-4-NH₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-456 3,5-Cl₂-4-NHC(O)OBu-t CF₃ 2-CH₃ CH₂CF₃ *1 5-457 3,5-Cl₂-4-NHC(O)OBu-t CF₃ 2-CH₃ CH₂(D-47a) *1 5-458 3,4-Cl₂ CF₃ 2-CH₃ CH₂CF₃ 138.0-140.0 5-459 3,4-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CF₃ 165.0-167.0 5-460 3,4-Cl₂ CF₃ 2-CH₃ CH₂(D-22a) *2 5-461 3,4-Cl₂ CF₃ 2-CH₃ CH₂(D-47a) *2 5-462 3,5-Cl₂ CF₃ 2-Cl H *1 5-463 3,5-Cl₂ CF₃ 2-Cl CH₂C(O)NHCH₂CF₃ *1 5-464 3,5-Cl₂ CF₃ 2-Cl (D-50c)Cl 115.0-117.0 5-465 3,5-Cl₂ CF₃ 2-Br CH₂C(O)NHCH₂CF₃ 159.0-163.0 5-466 3,5-Cl₂ CF₃ 2-Br (D-57d)Cl 172.0-174.0 5-467 3,5-Cl₂ CF₃ 2-I H 126.0-128.0 5-468 3,5-Cl₂ CF₃ 2-I CH₂C(O)NHCH₂CF₃ *1 5-469 3,5-Cl₂ CF₃ 2-I (D-47d)Cl 125.0-128.0 5-470 3,5-Cl₂ CF₃ 2-I (D-50c)Cl *1 5-471 3,5-Cl₂ CF₃ 2-CH₃ CH₃ *1 5-472 3,5-Cl₂ CF₃ 2-CH₃ CH₂CHF₂ *1 5-473 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ *1 5-474 3,5-Cl₂ CF₃ 2-CH₃ CH₂OEt *1 5-475 3,5-Cl₂ CF₃ 2-CH₃ CH₂OPr-n *1 5-476 3,5-Cl₂ CF₃ 2-CH₃ CH₂OPr-i *1 5-477 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CH₂Cl *1 5-478 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CHF₂ *1 5-479 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CHCl₂ *1 5-480 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CF₃ 111.0-114.0 5-481 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CCl₃ *1 5-482 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CH₂OCH₃ *1 5-483 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂OH═CH₂ *1 5-484 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂C≡CH *1 5-485 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂Ph *1 5-486 3,5-Cl₂ CF₃ 2-CH₃ CH₂OC(O)CH₃ *1 5-487 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)OH *1 5-488 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)OCH₂CF₃ *1 5-489 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₂CF₃ 156.0-159.0 5-490 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₂CH₂OCH₂CH₂OCH₃ *2 5-491 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OH 160.0-164.0 5-492 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OC(O)CH₃ *1 5-493 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OC(O)NHCH₂CH₂Cl *1 5-494 3,5-Cl₂ CF₃ 2-CH₃ E-4a 144.0-147.0 5-495 3,5-Cl₂ CF₃ 2-CH₃ E-5a(R) *1 5-496 3,5-Cl₂ CF₃ 2-CH₃ E-23a *1 5-497 3,5-Cl₂ CF₃ 2-CH₃ CH₂SCH₃ *1 5-498 3,5-Cl₂ CF₃ 2-CH₃ CH₂S(O)CH₃ 159.0-161.0 5-499 3,5-Cl₂ CF₃ 2-CH₃ CH₂SC₂CH₃ 207.0-209.0 5-500 3,5-Cl₂ CF₃ 2-CH₃ CH₂SC(O)CH₃ *1 5-501 3,5-Cl₂ CF₃ 2-CH₃ CH₂SC(S)OEt *1 5-502 3,5-Cl₂ CF₃ 2-CH₃ CH₂SO₂OH·Q5 *1 5-503 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SC(O)NHEt 148.0-150.0 5-504 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SC(O)NH(Ph-4-F) *2 5-505 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂S(D-50a) *2 5-506 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SO₂(D-50a) *2 5-507 3,5-Cl₂ CF₃ 2-CH₃ CH₂NH₂·Q1 155.0-157.0 5-508 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHEt *1 5-509 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHCH₂CF₃ *1 5-510 3,5-Cl₂ CF₃ 2-CH₃ CH₂N(CH₂CF₃)C(O)CH₃ *1 5-511 3,5-Cl₂ CF₃ 2-CH₃ CH₂N(CH₂CF₃)C(O)OCH₃ *1 5-512 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)CH₃ 112.0-114.0 5-513 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)CF₃ 191.0-194.0 5-514 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)CH₂CF₃ 212.0-217.0 5-515 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)OCH₃ *1 5-516 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)OEt 110.0-120.0 5-517 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)OCH₂CF₃ 118.0-119.0 5-518 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)NHEt 152.0-154.0 5-519 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)NHC(O)OCH₃ 88.0-90.0 5-520 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHC(O)OCH₂CH₂Cl 96.0-99.0 5-521 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHSO₂Et *1 5-522 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂CF₃ *1 5-523 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH═NOCH₃ *1 5-524 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₂OH)C(O)OCH₃ *1 5-525 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂CH₂C(O)OEt *1 5-526 3,5-Cl₂ CF₃ 2-CH₃ E-7e 192.0-194.5 5-527 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)Et *1 5-528 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(Et)₂ *1 5-529 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPr-c 146.0-147.0 5-530 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-s 148.0-149.0 5-531 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂Pr-c 195.0-197.0 5-532 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂OH(OEt)₂ *1 5-533 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CN 198.0-201.0 5-534 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂C(O)NHCH₃ 170.0-172.0 5-535 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂C(O)NHOH₂CF₃ 180.0-183.0 5-536 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NH(Ph-4-F) 235.0-237.0 5-537 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NH(Ph-4-CN) 267.0-269.0 5-538 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NH₂ *1 5-539 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH₂Cl(D) 162.0-164.0 5-540 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH₂Cl(L) 149.0-151.0 5-540(+) 99% d.e. [α]_(D) ^(22.9) + 54.77° (EtOH, c = 0.652) 103.0-105.0 5-541 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CF₃(D) 188.0-190.0 [α]_(D) ^(24.7) + 14.89° (EtOH, c = 0.744) 5-541(R) 95% d.e. [α]_(D) ^(24.9) − 54.42° (EtOH, c = 0.890) 164.0-166.0 5-541(S) 95% d.e. [α]_(D) ^(24.9) + 50.27° (EtOH, c = 0.650) 216.0-217.0 5-542 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CF₃(L) 181.0-183.0 5-543 3,5-Cl₂ CF₃ 2-CH₃ CH(Et)C(O)NHCH₂CF₃ 197.0-205.0 5-544 3,5-Cl₂ CF₃ 2-CH₃ CH(Pr-i)C(O)NHCH₂CF₃ 220.0-224.0 5-545 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂CH₂C(O)NHCH₂CF₃ 172.0-175.0 5-546 3,5-Cl₂ CF₃ 2-CH₃ T-50 *2 5-547 3,5-Cl₂ CF₃ 2-CH₃ T-51 *2 5-548 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-14b)CF₃ *1 5-549 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-17b)CF₃ 219.0-222.0 5-550 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-21e) 71.0-79.0 5-551 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q1 177.0-177.5 5-552 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q2 95.0-103.0 5-553 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q3 135.0-137.0 5-554 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q4 125.0-130.0 5-555 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)SCH₃ *1 5-556 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)SO₂CH₃ *1 5-557 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)CF₃ *1 5-558 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-37a) *2 5-559 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-61b) *1 5-560 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-14a) *1 5-561 3,5-Cl₂ CF₃ 2-CH₃ OCH₃ *1 5-562 3,5-Cl₂ CF₃ 2-CH₃ OCH₂CH═CH₂ 158.0-160.0 5-563 3,5-Cl₂ CF₃ 2-CH₃ SO₂CH₃ *1 5-564 3,5-Cl₂ CF₃ 2-CH₃ SO₂N(CH₃)₂ *2 5-565 3,5-Cl₂ CF₃ 2-CH₃ N(Ph)C(O)CH₂Cl *1 5-566 3,5-Cl₂ CF₃ 2-CH₃ N═CHN(CH₃)₂ 100.0-106.0 5-567 3,5-Cl₂ CF₃ 2-CH₃ N═C(CH₃)N(CH₃)₂ 79.0-84.0 5-568 3,5-Cl₂ CF₃ 2-CH₃ CHO 179.0-181.0 5-569 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₂CF₃ 148.0-150.0 5-570 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH₂F 144.0-146.0 5-571 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CHF₂ 165.0-168.0 5-572 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH(CH₂F)₂ *1 5-573 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH(CH₂F)CH₂Cl *1 5-574 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₃ 161.0-163.0 5-575 3,5-Cl₂ CF₃ 2-CH₃ C(O)N(CH₃)₂ *2 5-576 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHEt 178.0-180.0 5-577 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂CH₂Cl 210.0-213.0 5-578 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂C(O)NHCH₂CF₃ 231.0-232.0 5-579 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂CH═CH₂ 160.0-162.0 5-580 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂(Ph-4-F) 101.0-104.0 5-581 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂(D-47a) *1 5-582 3,5-Cl₂ CF₃ 2-CH₃ C(O)NH(Ph-4-F) 188.0-191.0 5-583 3,5-Cl₂ CF₃ 2-CH₃ C(O)(T-33) *2 5-584 3,5-Cl₂ CF₃ 2-CH₃ O(S)NHCH₃ 98.0-101.0 5-585 3,5-Cl₂ CF₃ 2-CH₃ Ph *1 5-586 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-F 164.0-167.0 5-587 3,5-Cl₂ CF₃ 2-CH₃ Ph-3-F 163.0-171.0 5-588 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-F *1 5-589 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-Cl 165.0-169.0 5-590 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-CF₃ 95.0-99.0 5-591 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-OH *1 5-592 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-OCH₃ 180.0-182.0 5-593 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-OCF₃ 165.0-167.0 5-594 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-OSO₂CH₃ 160.0-163.0 5-595 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-SCH₃ 181.0-183.0 5-596 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-S(O)CH₃ 119.0-126.0 5-597 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-SO₂CH₃ 222.0-225.0 5-598 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-SO₂NH₂ 126.0-130.0 5-599 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-NO₂ 141.0-148.0 5-600 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-CN 168.0-175.0 5-601 3,5-Cl₂ CF₃ 2-CH₃ Ph-3-CN *1 5-602 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)NH₂ 209.0-213.0 5-603 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-C(O)NHPr-i *1 5-604 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,4-F₂ *1 5-605 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,5-F₂ *1 5-606 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,6-F₂ 177.5-181.0 5-607 3,5-Cl₂ CF₃ 2-CH₃ Ph-3,4-F2 154.0-160.0 5-608 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-F-4-Cl 140.0-142.0 5-609 3,5-Cl₂ CF₃ 2-CH₃ Ph-3,4-Cl₂ *1 5-610 3,5-Cl₂ CF₃ 2-CH₃ Ph-3,5-Cl₂ *1 5-611 3,5-Cl₂ CF₃ 2-CH₃ Ph-3-NO₂-4-F *1 5-612 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,4,6-F₃ *1 5-613 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,6-F2-4-Br 215.0-217.0 5-614 3,5-Cl₂ CF₃ 2-CH₃ D-3a 102.0-107.0 5-615 3,5-Cl₂ CF₃ 2-CH₃ D-5a *1 5-616 3,5-Cl₂ CF₃ 2-CH₃ (D-10b)CH₃ 190.0-193.0 5-617 3,5-Cl₂ CF₃ 2-CH₃ D-14a *1 5-618 3,5-Cl₂ CF₃ 2-CH₃ (D-14c)Br *1 5-619 3,5-Cl₂ CF₃ 2-CH₃ (D-21b)CF₃ *1 5-620 3,5-Cl₂ CF₃ 2-CH₃ D-21e 182.0-187.0 5-621 3,5-Cl₂ CF₃ 2-CH₃ D-61b *1 5-622 3,5-Cl₂ CF₃ 2-CH₃ D-41a 223.0-224.0 5-623 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)Cl 129.0-132.5 5-624 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)Br 181.0-183.0 5-625 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)I 180.0-186.0 5-626 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)CH₃ 110.0-113.0 5-627 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)CF₃ 184.0-186.0 5-628 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)NO₂ 113.0-116.0 5-629 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)CN *1 5-630 3,5-Cl₂ CF₃ 2-CH₃ (D-47e)Cl *1 5-631 3,5-Cl₂ CF₃ 2-CH₃ (D-47e)Br *1 5-632 3,5-Cl₂ CF₃ 2-CH₃ (D-47f)-3,5-Cl₂ 120.0-124.0 5-633 3,5-Cl₂ CF₃ 2-CH₃ (D-48e)Cl *1 5-634 3,5-Cl₂ CF₃ 2-CH₃ (D-48e)CN *1 5-635 3,5-Cl₂ CF₃ 2-CH₃ (D-49b)Cl *1 5-636 3,5-Cl₂ CF₃ 2-CH₃ D-49e 173.0-177.0 5-637 3,5-Cl₂ CF₃ 2-CH₃ (D-50b)CH₃ *1 5-638 3,5-Cl₂ CF₃ 2-CH₃ (D-50c)Cl 137.0-141.0 5-639 3,5-Cl₂ CF₃ 2-CH₃ (D-50c)Br 178.0-181.0 5-640 3,5-Cl₂ CF₃ 2-CH₃ (D-50c)I *1 5-641 3,5-Cl₂ CF₃ 2-CH₃ (D-51c)Cl 85.0-87.0 5-642 3,5-Cl₂ CF₃ 2-CH₃ D-52a 207.0-211.0 5-643 3,5-Cl₂ CF₃ 2-CH₃ D-53a 139.0-144.0 5-644 3,5-Cl₂ CF₃ 2-CH₃ (D-53b)Br 251.0-253.0 5-645 3,5-Cl₂ CF₃ 2-CH₃ (D-54b)Cl 99.0-102.5 5-646 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂0(O)NHCH₂CF₃ 171.0-173.0 5-647 3,5-Cl₂-4-CH₃ CF₃ 2-CH₃ CH₂CF₃ *2 5-648 3,5-Cl₂-4-CH₃ CF₃ 2-CH₃ CH₂(D-47a) *2 5-649 3,5-Cl₂-4-OH CF₃ 2-CH₃ CH₂(D-47a) *2 5-650 3,5-Cl₂-4-OCH₃ CF₃ 2-CH₃ CH₂CF₃ 198.0-199.0 5-651 3,5-Cl₂-4-OCH₃ CF₃ 2-CH₃ CH₂(D-47a) *2 5-652 3,5-Cl₂-4-OC(O)OBu-t CF₃ 2-CH₃CH₂(D-47a) *2 5-653 3,5-Cl₂-4-N(CH₃)2 CF₃ 2-CH₃ CH₂CF₃ *2 5-654 3,5-Cl₂-4-N(CH₃)2 CF₃ 2-CH₃ CH₂(D-47a) *2 5-655 3,5-Cl₂ CF₃ 2-I CH₂OCH₂CF₃ *1 5-656 3,5-Cl₂ CF₃ 2-I E-4a *1 5-657 3,5-Cl₂ CF₃ 3-I CH₂C(O)NHCH₂CF₃ *1 5-658 3,5-Cl₂ CF₃ 2-CH₃ (E-23b)OCH₃ *1 5-659 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NH(E-4a) 86.0-91.0 5-660 3,5-Cl₂ CF₃ 2-CH₃ CH═CH₂ *1 5-661 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CBr 166.0-169.0 5-662 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)C(O)NHCH₂CF₃ *1 5-663 3,5-Cl₂ CF₃ 2-CH₃ OC(O)NHCH₂CF₃ 111.0-114.0 5-664 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ 151.0-154.5 5-665 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et 169.0-172.0 5-666 3,5-Cl₂ CF₃ 2-CH₃ D-22a 228.0-230.0 5-667 3,5-Cl₂ CF₃ 2-CH₃ (D-22b)Br *1 5-668 3,5-Cl₂ CF₃ 2-CH₃ (D-47b)Cl *1 5-669 3,5-Cl₂ CF₂Cl 2-Cl H *1 5-670 3-Cl-5-Br CF₃ 2-CH₃ H *1 5-671 3,5-Br₂ CF₃ 2-Cl H 105.0-1 08.0 5-672 3,5-(CF₃)₂ CF₃ 2-CH₃ H *1 5-673 3,5-Cl₂ CF₃ 2-CH₃ D-2a 105.0-110.0 5-674 3,5-Cl₂ CF₃ 2-CH₃ (D-50c)CN 118.0-121.0 5-675 3,5-Cl₂ CF₃ 2-CH₃ (D-52b)Cl 231.0-234.0 5-676 3,5-Cl₂ CF₃ 2-CH₃ (D-53b)Cl 242.0-243.0 5-677 3,5-Cl₂ CF₃ 2-Et H *1 5-678 3,5-Cl₂ CF₃ 2-CH₂OCH₃ H 186.0-188.0 5-679 3,5-Cl₂ CF₃ 2-OCHF₂ H *1 5-680 3,5-Cl₂ CF₃ 2-NO₂ H *1 5-681 3,5-Cl₂ CF₃ 2-NH₂ H 190.0-193.0 5-682 3,5-Cl₂ CF₃ 2-NHC(O)CH₃ H *1 5-683 3,4,5-Cl₃ CF₃ 2-CH₃ H 153.0-155.0 5-684 3-Cl-5-CF₃ CF₃ 2-CH₃ CH₂CF₃ *1 5-685 3,5-Cl₂-4-F CF₃ 2-CH₃ CH₂CF₃ *1 5-686 3-Cl-4-F-5-CF₃ CF₃ 2-CH₃ CH₂CF₃ *1 In Table above, the indications of “5-529 (R)*” and “5-529 (S)*” show optical isomers in which the absolute configuration of 5-position of 4,5-dihydroisooxazole ring is R- and S-configuration, respectively.

TABLE 12

No. (X)_(m) R³ (Y)_(n) R² R¹ m.p. (° C.) 6-001 3,5-Cl₂ CF₃ 2-Cl Et Et *1 6-002 3,5-Cl₂ CF₃ 2-CH₃ NH₂ CH₃ 138.0-139.0 6-003 3,5-Cl₂ CF₃ 2-CH₃ Et Et *1 6-004 3,5-Cl₂ CF₃ 2-CH₃ NH₂ Et 76.0-78.0 6-005 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₃ Et *1 6-006 3,5-Cl₂ CF₃ 2-CH₃ N═C(CH₃)₂ Et *1 6-007 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN n-Bu *1 6-008 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN CH₂CN *1 6-009 3,5-Cl₂ CF₃ 2-CH₃ OH CH₂Ph 175.0-177.0 6-010 3,5-Cl₂ CF₃ 2-CH₃ OCH₃ CH₂Ph *1 6-011 3,5-Cl₂ CF₃ 2-CH₃ OC(O)CH₃ CH₂Ph *1 6-012 3,5-Cl₂ CF₃ 2-CH₃ OC(O)OCH₃ CH₂Ph *1 6-013 3,5-Cl₂ CF₃ 2-CH₃ OSO₂CH₃ CH₂Ph *1 6-014 3,5-Cl₂ CF₃ 2-CH₃ NH₂ CH₂Ph 135.0-136.0 6-015 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN CH₂(D-22a) *1 6-016 3,5-Cl₂ CF₃ 2-CH₃ CH₂═CH CH₂(D-22a) *1 6-017 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(D-22a) *1 6-018 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et CH₂(D-22a) *1 6-019 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-22a) *1 6-020 3,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₂(D-47a) *1 6-021 3,5-Cl₂ CF₃ 2-CH₃ Et CH₂(D-47a) *1 6-022 3,5-Cl₂ CF₃ 2-CH₃ n-Pr CH₂(D-47a) *1 6-023 3,5-Cl₂ CF₃ 2-CH₃ i-Pr CH₂(D-47a) *1 6-024 3,5-Cl₂ CF₃ 2-CH₃ c-Pr CH₂(D-47a) *1 6-025 3,5-Cl₂ CF₃ 2-CH₃ t-Bu CH₂(D-47a) *1 6-026 3,5-Cl₂ CF₃ 2-CH₃ CH₂CF₃ CH₂(D-47a) *1 6-027 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ CH₂(D-47a) *1 6-028 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₃ CH₂(D-47a) *1 6-029 3,5-Cl₂ CF₃ 2-CH₃ CH₂SCH₃ CH₂(D-47a) *1 6-030 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OCH₃ CH₂(D-47a) *1 6-031 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN CH₂(D-47a) *1 6-032 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═CH₂ CH₂(D-47a) *1 6-033 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CH CH₂(D-47a) *1 6-034 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(D-47a) *1 6-035 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et CH₂(D-47a) *1 6-036 3,5-Cl₂ CF₃ 2-CH₃ C(O)Pr-n CH₂(D-47a) *1 6-037 3,5-Cl₂ CF₃ 2-CH₃ C(O)Pr-i CH₂(D-47a) *1 6-038 3,5-Cl₂ CF₃ 2-CH₃ C(O)Pr-c CH₂(D-47a) *1 6-039 3,5-Cl₂ CF₃ 2-CH₃ C(O)Bu-t CH₂(D-47a) *1 6-040 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₂OCH₃ CH₂(D-47a) 53.0-55.0 6-041 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH═CH₂ CH₂(D-47a) *1 6-042 3,5-Cl₂ CF₃ 2-CH₃ C(O)Ph CH₂(D-47a) *1 6-043 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-47a) *1 6-044 3,5-Cl₂ CF₃ 2-CH₃ C(O)OEt CH₂(D-47a) *1 6-045 3,5-Cl₂ CF₃ 2-CH₃ C(O)OPr-i CH₂(D-47a) *1 6-046 3,5-Cl₂ CF₃ 2-CH₃ C(O)OBu-i CH₂(D-47a) *1 6-047 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH₂Cl CH₂(D-47a) *1 6-048 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH₂OCH₃ CH₂(D-47a) *1 6-049 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH═CH₂ CH₂(D-47a) *1 6-050 3,5-Cl₂ CF₃ 2-CH₃ C(O)SCH₃ CH₂(D-47a) *1 6-051 3,5-Cl₂ CF₃ 2-CH₃ SO₂CH₃ CH₂(D-47a) *1 6-052 3,5-Cl₂ CF₃ 2-CH₃ NH₂ CH₂(D-47a) 126.0-130.0 6-053 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)₂ CH₂(D-47a) *1 6-054 3,5-Cl₂ CF₃ 2-CH₃ Et CH₂(D-48e)Cl *1 6-055 3,5-Cl₂ CF₃ 2-CH₃ c-Pr CH₂(D-49a) *1 6-056 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et CH₂(D-50a) *1 6-057 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂SCH₂CH_(2—) 209.5-211.5 6-058 3,5-Cl₂ CF₃ 2-CH₃ CH₃ N(CH₃)Ph 153.0-154.0 6-059 3,5-Cl₂ CF₃ 2-CH₃ Et N(CH₃)Ph 78.0-79.0 6-060 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ N(CH₃)Ph 72.0-73.0 6-061 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═CH₂ N(CH₃)Ph 76.0-77.0 6-062 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CH N(CH₃)Ph 83.0-84.0 6-063 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN N(CH₃)Ph 69.0-70.0 6-064 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ N(CH₃)Ph 82.0-83.0 6-065 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ N(CH₃)Ph 70.0-71.0 6-066 3,5-Cl₂ CF₃ 2-CH₃ CH₃ NH(D-50a) 107.0-109.0 6-067 3,5-Cl₂ CF₃ 2-CH₃ Et NH(D-50a) 185.0-187.0 6-068 3,5-Cl₂ CF₃ 2-CH₂— H 234.0-236.0 6-069 3,5-Cl₂ CF₃ 2-CH₂— CH₃ *1 6-070 3,5-Cl₂ CF₃ 2-CH₂— CH₂(D-47a) *1 6-071 3,5-Cl₂ CF₃ 2-N(CH₃)CH₂— CH₂(D-47a) *1 6-072 3,5-Cl₂ CF₃ 2-N═CH— H 249.0-251.0 6-073 3,5-Cl₂ CF₃ 2-N═CH— CH₂(D-47a) *1 6-074 3,5-Cl₂ CF₂Cl 2-CH₃ C(O)CH₃ CH₂CF₃ *1 6-075 3,5-Br₂ CF₃ 2-CH₃ C(O)CH₃ CH₂CF₃ *1 6-076 3,5-Br₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(D-47a) *1 6-077 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂CF₃ *2 6-078 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ CH₂(D-22a) *1 6-079 3,5-Cl₂ CF₃ 2-CH₃ CH₂OEt CH₂(D-47a) *1 6-080 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH(CH₃)(D-47a) *2 6-080(+)* 98% e.e [α]_(D) ^(22.4) +35.40° (CHCL₃, c = 0.397) *2 6-080(−)* 99% e.e [α]_(D) ^(22.2) −37.20° (CHCl₃, c = 0.473) *2 6-081 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ N(CH₃)(D-47a) *1 6-082 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ N(CH₃)(D-47a) *1 6-083 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ N(CH₃)(D-50a) *2 6-084 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ N(CH₃)(D-50a) *1 6-085 3,5-Cl₂ CF₃ 2-CH₃ —C(O)CH₂CH₂CH₂— *1 6-086 3,5-Cl₂ CF₃ 2-CH₃ —C(O)CH₂CH₂C(O)— *1 6-087 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(Ph)CH₂CH_(—) 84.0-88.0 6-088 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(D-47a)CH₂CH_(—) 87.0-92.0 6-089 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et CH₃ *1 6-090 3,5-Cl₂ CF₃ 2-CH₃ C(O)CF₃ CH₃ 181.0-183.0 6-091 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH₂CF₃ CH₃ 148.0-150.0 6-092 3,5-Cl₂ CF₃ 2-CH₃ CH₂OEt CH₂OEt *1 6-093 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂OEt *1 6-094 3,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₂OCH₂CF₃ *1 6-095 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂OCH₂CF₃ *1 6-096 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂CH₂OCH₃ *1 6-097 3,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₂(E-10a) *1 6-098 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(E-10a) *1 6-099 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(E-10a) *1 6-100 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ E-4a *1 6-101 3,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₂CH═NOCH₃ *1 6-102 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂CH═NOCH₃ *1 6-103 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂CH═NOCH₃ *1 6-104 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂C(O)NHCH₂CF₃ 115.0-120.0 6-105 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(Ph-4-OCH₃) *1 6-106 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(Ph-4-NO₂) *1 6-107 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(Ph-4-Ph) *1 6-108 3,5-Cl₂ CF₃ 2-CH₃ C(O)OBu-t CH₂(D-14b)CF₃ *1 6-109 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-61b) *1 6-110 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-47a)·Q1 70.0-100.0 6-111 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-F CH₂(D-47a) *1 6-112 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-50a) *1 6-113 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂CH₂CH[C(O)NHCH₂CF₃]— *1 6-114 3,5-Cl₂ CF₃ 2-CH₃ —CH₂OCH₂CH₂— *1 6-115 3,5-Cl₂ CF₃ 2-CH₃ —CH₂SCH₂CH₂— *1 6-116 3,5-Cl₂ CF₃ 2-CH₃ —CH₂SO₂CH₂CH₂— 206.0-208.0 6-117 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂OCH₂CH₂— 217.0-219.0 6-118 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂SO₂CH₂CH₂— 223.0-226.0 6-119 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(CH₃)CH₂CH₂— *1 6-120 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ OCH₃ *1 6-121 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ N(CH₃)2 *1 6-122 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ C(O)CH₃ *1 6-123 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH(CH₂F)OC(O)— *1 6-124 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ C(O)N(CH₃)₂ *1 6-125 3,5-Cl₂ CF₃ 2-CH₃ CH₃ C(O)NHEt *1 6-126 3,5-Cl₂ CF₃ 2-CH₃ CH₃ C(O)NHCH₂CF₃ *1 6-127 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(CH₂CF₃)C(O)— 167.0-170.0 6-128 3,5-Cl₂ CF₃ 2-C(═CH₂)— CH₂CF₃ 141.0-144.0 6-129 3,5-Cl₂ CF₃ 2-CH₃ CH₃ E-4a 155.0-157.0 6-130 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ E-4a *1 6-131 3,5-Cl₂ CF₃ 2-CH₃ O(O)Et E-4a *1 6-132 3,5-Cl₂ CF₃ 2-CH₃ C(O)Pr-i E-4a *1 6-133 3,5-Cl₂ CF₃ 2-CH₃ CH₃ E-6a 146.0-151.0 6-134 3,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₃ 166.5-168.5 In Table above, the indications of “6-080 (+)*” and “6-080 (−)*” show optically active forms of 1-(2-pyridyl) ethylamine moiety.

TABLE 13

No. (X)_(m) R³ (Y)_(n) R² R¹ m.p. (° C.) 7-001 3,5-Cl₂ CF₃ — H H 227.0-232.0 7-002 3,5-Cl₂ CF₃ — H CH₂CF₃ *1 7-003 3,5-Cl₂ CF₃ — H CH₂(D-22a) *1 7-004 3,5-Cl₂ CF₃ — H CH₂(D-47a) 165.0-167.0 7-005 3,5-Cl₂ CF₃ 2-F H CH₂(D-22a) 171.0-173.0 7-006 3,5-Cl₂ CF₃ 2-Cl H CH₂(D-22a) 90.0-92.0 7-007 3,5-Cl₂ CF₃ 2-CH₃ H CH₂CF₃ *1 7-008 3,5-Cl₂ CF₃ 2-CH₃ H CH₂(D-22a) *1 7-009 3,5-Cl₂ CF₃ 2-CH₃ H CH₂(D-47a) *1 7-010 3,5-Cl₂ CF₃ 2-CH₃ H N(CH₃)Ph 100.0-111.0

TABLE 14

No. (X)_(m) R³ (Y)_(n) R^(1a) R^(2a) m.p. (° C.) 8-001 3,5-Cl₂ CF₃ — —N(CH₃)CH═CHS— *1 8-002 3,5-Cl₂ CF₃ 2-CH₃ —N(CH₃)CH═CHS— *1 8-003 3,5-Cl₂ CF₃ 2-CH₃ —N(Pr-n)CH═CHS— *1 8-004 3,5-Cl₂ CF₃ 2-CH₃ —N(CH₃)N═CHCH₂S— *1 8-005 3,5-Cl₂ CF₃ 2-CH₃ O —N(CH₃)CH═CHCH═N— *1 8-006 3,5-Cl₂ CF₃ 2-CH₃ O —N(CH₃)N═CHS— *1 8-007 3,5-Cl₂ CF₃ 2-CH₃ O —N(CH₃)N═CClCH═CH— *2

TABLE 15

No. G (X)_(m) R³ (Y)_(n) R² R¹ m.p. (° C.) 9-001 G-3 6-F CF₃ — H CH₂CF₃ 175.0-177.0 9-002 G-3 6-Cl CF₃ — H CH₂CF₃ 192.0-195.0 9-003 G-3 5-Br CF₃ 2-CH₃ H CH₂CF₃ *1 9-004 G-3 6-OCH₃ CF₃ — H CH₂CF₃ 150.0-152.0 9-005 G-6 4,6-Cl₂ CF₃ — H CH₂CF₃ 140.0-142.0 9-006 G-6 4,6-Cl₂ CF₃ 2-CH₃ H CH₂CF₃ 131.0-134.0 9-007 G-18 — CF₃ — H CH₂CF₃ 156.0-157.0 9-008 G-20 4-CF₃ CF₃ 2-CH₃ H CH₂CF₃ *1 9-009 G-20 4-CF₃ CF₃ 2-CH₃ H CH₂(D-47a) *1 9-010 G-13 5-Cl CF₃ 2-CH₃ H CH₂CF₃ *1 9-011 G-13 5-Cl CF₃ 2-CH₃ H CH₂(D-47a) *1 Substituent G in the above-mentioned formula is the structure of G-3, G-6, G-18 or G-20 mentioned below.

TABLE 16

No. (X)_(m) A¹ A² A³ (Y)_(n) R¹ m.p. (° C.) 10-001 3,5-Cl₂ N C C — CH₂CF₃ *1 10-002 3,5-Cl₂ N C C — CH₂(D-47a) *1 10-003 3,5-Cl₂ N(O) C C — CH₂CF₃ *1 10-004 3,5-Cl₂ C N C — CH₂CF₃ *1 10-005 3,5-Cl₂ C N C — CH₂(D-47a) *1

TABLE 17

No. (X)_(m) R³ (Y)_(n) R m.p. (° C.) 11-001 3-Cl CF₃ — C(O)OH 220.0-225.0 11-002 3-Cl CF₃ — C(O)OCH₃ 100.0-101.0 11-003 4-Cl CF₃ — C(O)OH 255.0-257.0 11-004 4-Cl CF₃ — C(O)OCH₃ *1 11-005 3-I CF₃ 2-CH₃ C(O)OH 169.0-172.0 11-006 3-I CF₃ 2-CH₃ C(O)OCH₃ *1 11-007 3-NO₂ CF₃ 2-CH₃ C(O)OCH₃ *1 11-008 3,4-F₂ CF₃ — C(O)OH 246.0-248.0 11-009 3,4-F₂ CF₃ — C(O)OCH₃ 132.0-133.0 11-010 2,4-Cl₂ CF₃ — C(O)OH 104.0-106.0 11-011 2,4-Cl₂ CF₃ — C(O)OCH₃ 103.0-106.0 11-012 2,5-Cl₂ CF₃ — C(O)OH 97.0-100.0 11-013 2,5-Cl₂ CF₃ — C(O)OCH₃ 163.0-165.0 11-014 3,4-Cl₂ H — C(O)OCH₃ 115.0-117.0 11-015 3,4-Cl₂ CH₃ — C(O)OCH₃ 98.0-100.0 11-016 3,4-Cl₂ CF₃ — C(O)OH 215.0-217.0 11-017 3,4-Cl₂ CF₃ — C(O)OCH₃ 95.0-97.0 11-018 3,4-Cl₂ CF₃ — C(O)OBu-t 94.0-95.0 11-019 3,4-Cl₂ CF₃ — C(O)OCH₂Ph 94.0-95.0 11-020 3,4-Cl₂ Ph — C(O)OCH₃ 143.0-145.0 11-021 3,5-Cl₂ CF₃ — CH₂OH 108.0-110.0 11-022 3,5-Cl₂ CF₃ — OH 153.0-155.5 11-023 3,5-Cl₂ CF₃ — OCH₃ 93.0-96.5 11-024 3,5-Cl₂ CF₃ — NO₂ 161.0-162.0 11-025 3,5-Cl₂ CF₃ — NH₂ 98.0-99.0 11-026 3,5-Cl₂ CF₃ — CN 140.0-142.0 11-027 3,5-Cl₂ CF₃ — O(O)OH 237.0-240.0 11-028 3,5-Cl₂ CF₃ — O(O)OCH₃ 94.0-96.0 11-029 3,5-Cl₂ CF₃ 2-F CH₂Br *2 11-030 3,5-Cl₂ CF₃ 2-F CH₂OC(O)CH₃ *2 11-031 3,5-Cl₂ CF₃ 2-F CH₂OH *1 11-032 3,5-Cl₂ CF₃ 2-F C(O)OH 172.0-174.0 11-033 3,5-Cl₂ CF₃ 3-F Br 136.0-138.0 11-034 3,5-Cl₂ CF₃ 3-F C(O)OH *1 11-035 3,5-Cl₂ CF₃ 3-F C(O)OEt 94.0-96.0 11-036 3,5-Cl₂ CF₃ 2-Cl OSO₂CF₃ 154.0-157.5 11-037 3,5-Cl₂ CF₃ 2-Cl C(O)OH 150.0-151.0 11-038 3,5-Cl₂ CF₃ 2-Cl C(O)OCH₃ *2 11-039 3,5-Cl₂ CF₃ 3-Cl Br *2 11-040 3,5-Cl₂ CF₃ 3-Cl C(O)OH 187.0-188.0 11-041 3,5-Cl₂ CF₃ 3-Cl C(O)OEt *1 11-042 3,5-Cl₂ CF₃ 2-Br C(O)OCH₃ 83.0-86.0 11-043 3,5-Cl₂ CF₃ 2-I CH₃ 130.0-132.0 11-044 3,5-Cl₂ CF₃ 2-I CH₂Br *1 11-045 3,5-Cl₂ CF₃ 2-I CH₂OC(O)CH₃ *1 11-046 3,5-Cl₂ CF₃ 2-I CH₂OH *1 11-047 3,5-Cl₂ CF₃ 2-I C(O)OH *1 11-048 3,5-Cl₂ CF₃ 2-I C(O)OCH₃ *2 11-049 3,5-Cl₂ CF₃ 2-CH₃ NO₂ 135.0-136.0 11-050 3,5-Cl₂ CF₃ 2-CH₃ NH₂ *1 11-051 3,5-Cl₂ CF₃ 2-CH₃ F 67.0-68.0 11-052 3,5-Cl₂ CF₃ 2-CH₃ Br 113.0-114.5 11-053 3,5-Cl₂ CF₃ 2-CH₃ C(O)OH 150.0-152.0 11-054 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ 96.0-99.5 11-055 3,5-Cl₂ CF₃ 2-CH₃ C(O)OEt n_(D) ^(21. 4 °C.)1.5474 11-056 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂(D-47a) *2 11-057 3,5-Cl₂ CF₃ 2-CH₃ C(O)(D-14a) *1 11-058 3,5-Cl₂ CF₃ 2-CH₃ C(O)(D-38a) 58.0-59.0 11-059 3,5-Cl₂ CF₃ 2-Et C(O)OCH₃ *2 11-060 3,5-Cl₂ CF₃ 2-CH₂Br C(O)OCH₃ *2 11-061 3,5-Cl₂ CF₃ 2-CF₃ F *1 11-062 3,5-Cl₂ CF₃ 2-CF₃ CN *1 11-063 3,5-Cl₂ CF₃ 2-CF₃ C(O)OCH₃ *2 11-064 3,5-Cl₂ CF₃ 2-OH NO₂ 110.0-113.0 11-065 3,5-Cl₂ CF₃ 2-OH NH₂ 178.0-181.0 11-066 3,5-Cl₂ CF₃ 2-OCH₃ OSO₂CF₃ *1 11-067 3,5-Cl₂ CF₃ 2-OCH₃ C(O)OH *1 11-068 3,5-Cl₂ CF₃ 2-OCH₃ C(O)OEt 142.0-144.0 11-069 3,5-Cl₂ CF₃ 2-OCF₃ NH₂ 81.5-84.0 11-070 3,5-Cl₂ CF₃ 2-OCF₃ I *1 11-071 3,5-Cl₂ CF₃ 2-OCF₃ C(O)OCH₃ *1 11-072 3,5-Cl₂ CF₃ 2-SCH₃ C(O)OH 151.0-152.0 11-073 3,5-Cl₂ CF₃ 2-SCH₃ C(O)OCH₃ *2 11-074 3,5-Cl₂ CF₃ 2-NO₂ Br 179.0-181.0 11-075 3,5-Cl₂ CF₃ 2-NO₂ C(O)OEt 160.0-162.0 11-076 3,5-Cl₂ CF₃ 2-NH₂ Br *2 11-077 3,5-Cl₂ CF₃ 2-NH₂ C(O)OH *2 11-078 3,5-Cl₂ CF₃ 2-NH₂ C(O)OEt *2 11-079 3,5-Cl₂ CF₃ 2-Ph C(O)OH *1 11-080 3,5-Cl₂ CF₃ 2-Ph C(O)OCH₃ *1 11-081 3,5-Cl₂ CF₃ 2,3-F₂ CH₃ *1 11-082 3,5-Cl₂ CF₃ 2,3-F₂ CH₂Br *1 11-083 3,5-Cl₂ CF₃ 2,3-F₂ CH₂OH *1 11-084 3,5-Cl₂ CF₃ 2,6-Cl₂ C(O)OEt *2 11-085 3,5-Cl₂ CF₃ 2-Cl-6-CH₃ NH₂ *1 11-086 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ OH 209.0-214.0 11-087 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ OSO₂CF₃ N_(D) ^(21. 6° C.)1.5194 11-088 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ C(O)OH 128.5-130.5 11-089 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ C(O)OCH₃ 135.0-138.0 11-090 3,5-Cl₂ CF₂Cl 2-Cl C(O)OH 100.0-104.5 11-091 3,5-Cl₂ CF₂Cl 2-CH₃ C(O)OH 76.0-80.0 11-092 3,5-Cl₂ CF₂Cl 2-CH₃ C(O)OEt *1 11-093 3,5-Br₂ CF₃ 2-Cl C(O)OH 144.5-147.0 11-094 3,5-Br₂ CF₃ 2-CH₃ C(O)OH 135.0-138.5 11-095 3,5-Br₂ CF₃ 2-CH₃ C(O)OEt *1 11-096 3-OCH₂O-4 CF₃ — CO(O)OH 208.0-210.0 11-097 3-OCH₂O-4 CF₃ — C(O)OCH₃ 172.0-173.0 11-098 3,5-Cl₂ CF₃ — Br 122.0-124.0 11-099 3,5-Cl₂ CF₃ — I 144.0-146.0 11-100 3,5-Cl₂ CF₃ — CH₂Cl 98.0-100.0 11-101 3,5-Cl₂ CF₃ 2-F CH₃ 87.0-89.0 11-102 3,5-Cl₂ CF₃ 2-F CHBr₂ *1 11-103 3,5-Cl₂ CF₃ 2-Cl CH₃ 97.0-99.0 11-104 3,5-Cl₂ CF₃ 2-Cl CH₂Br 94.0-97.0 11-105 3,5-Cl₂ CF₃ 2-Cl CHBr₂ *1 11-106 3,5-Cl₂ CF₃ 2-Cl CH₂OH 32.0-35.0 11-107 3,5-Cl₂ CF₃ 2-Cl CH₂OC(O)CH₃ *1 11-108 3,5-Cl₂ CF₃ 2-Cl NO₂ 97.0-103.0 11-109 3,5-Cl₂ CF₃ 2-Cl NH₂ 158.0-160.0 11-110 3,5-Cl₂ CF₃ 2-Cl CHO 129.0-130.0 11-111 3,5-Cl₂ CF₃ 2-Br CH₃ 119.0-121.0 11-112 3,5-Cl₂ CF₃ 2-Br CHBr₂ *1 11-113 3,5-Cl₂ CF₃ 2-Br CH₂OH *1 11-114 3,5-Cl₂ CF₃ 2-Br CH₂OC(O)CH₃ *1 11-115 3,5-Cl₂ CF₃ 2-I CHBr₂ 125.0-128.0 11-116 3,5-Cl₂ CF₃ 2-I CHO *1 11-117 3,5-Cl₂ CF₃ 2-CH₃ Cl 115.5-117.0 11-118 3,5-Cl₂ CF₃ 2-CH₃ CH₂Cl *1 11-119 3,5-Cl₂ CF₃ 2-CH₃ CH₂OH *1 11-120 3,5-Cl₂ CF₃ 2-CH₃ CN 141.0-142.0 11-121 3,5-Cl₂ CF₃ 2-CH₃ C(O)Cl 140.5-143.0 11-122 3,5-Cl₂ CF₃ 3-OH C(O)OEt *1 11-123 3,5-Cl₂ CF₃ 2-NO₂ F 86.0-89.0 11-124 3,5-(CF₃)₂ CF₃ — NO₂ 170.0-172.0 11-125 3,5-Cl₂ CF₃ 2-OCHF₂ NO₂ *1 11-126 3,5-Cl₂ CF₃ 2-OCHF₂ NH₂ *1 11-127 3,5-Cl₂ CF₃ 2-OCHF₂ I *1 11-128 3,5-Cl₂ CF₃ 2-NO₂ CH₃ 119.0-122.0 11-129 3-Cl-5-Br CF₃ 2-CH₃ C(O)OEt *1 11-130 3,5-(CF₃)₂ CF₃ 2-CH₃ C(O)OEt *2 11-131 3,5-Cl₂ CF₃ 2-OH CH₃ 145.0-147.0 11-132 3,5-Cl₂ CF₃ 2-OCH₃ CH₃ 86.0-89.0

TABLE 18

No. (X)_(m) R³ A¹ A² (Y)_(n) R m.p. (° C.) 12-001 3,5-Cl₂ CF₃ N C — Cl 139.0-140.0 12-002 3,5-Cl₂ CF₃ N C — Br 147.0-148.0 12-003 3,5-Cl₂ CF₃ N C — C(O)OH 118.0-120.0 12-004 3,5-Cl₂ CF₃ N C — C(O)OEt 154.0-155.0 12-005 3,5-Cl₂ CF₃ C N — C(O)OH 195.5-198.5 12-006 3,5-Cl₂ CF₃ C N — C(O)OCH₃ 147.0-151.5

TABLE 19

No. A¹ (Y)_(n) R² R¹ J m.p. (° C.) 13-001 C — H CH₂CF₃ H 153.0-154.0 13-002 C — H CH₂CF₃ Cl 158.0-160.0 13-003 C — H CH₂Ph H 191.0-192.0 13-004 C — H CH₂Ph Cl 131.0-133.0 13-005 C — H CH₂(D-47a) H 166.0-168.0 13-006 C 2-CH₃ H CH₂CF₃ H 190.5-194.0 13-007 C 2-CH₃ H CH₂CF₃ Cl 134.0-137.0 13-008 C 2-CH₃ H CH₂(D-47a) H 163.0-164.0 13-009 C 2-CH₃ H CH₂(D-47a) Cl 174.0-176.0 13-010 C 3-CH₃ H CH₂CF₃ H 163.0-168.0

TABLE 20

No. X¹ (X²)_(m1) R³ m.p./b.p. (° C.) 14-001 Cl 5-Cl Pr-i n_(D) ^(20. 6° C.)1.5472 14-002 Cl 5-Cl CHF₂ n_(D) ^(20. 6° C.)1.5370 14-003 Cl 5-Cl CF₃ 64.0-66.0/2 mmHg 14-004 Cl 5-Cl CF₂Cl *2 14-005 Cl 5-Cl CF₂CF₃ *2 14-006 Cl 5-Cl CH₂OCH₂CF₃ *2 14-007 Cl 5-Cl CH₂Si(CH₃)₃ *2 14-008 Cl 5-Cl D-47a *2 14-009 Cl 5-Br CF₃ *2 14-010 Cl 5-CH₃ CF₃ *2 14-011 Cl 5-CH₃-6-F CF₃ n_(D) ^(20. 6° C.)1.4895 14-012 Cl 4-F-5-Cl CF₃ *2 14-013 Cl 4,5-Cl₂ CF₃ *1 14-014 Cl 4-NHC(O)OBu-t-5-Cl CF₃ 67.0-68.0 14-015 Br — CF₃ n_(D) ^(20. 7° C.)1.5258 14-016 Br 5-Br CF₃ *2 14-017 CF₃ — CF₃ n_(D) ^(20. 6° C.)1.4228 14-018 CF₃ 5-Cl CF₃ *2 14-019 CF₃ 5-NO₂ CF₃ n_(D) ^(20. 6° C.)1.4553 14-020 CF₃ 4-F-5-Cl CF₃ *2 14-021 T-4 — CF₃ *2 14-022 OCF₂CHFOCF₂CF₂CF₃ — CF₃ *2 14-023 OCH₂Ph — CF₃ *2 14-024 OCH₂(Ph-2-Cl) — CF₃ *2 14-025 O[(D-47f)-3-Cl-5-CF₃] — CF₃ *2 14-026 SCF₃ — CF₃ *2 14-027 NO₂ — CF₃ *2

Among the compounds of the present invention, ¹H NMR data of the compounds that the measured value of molecular ion peak, melting point or refractive index is not shown are shown in Table 21.

In the meantime, the indication of “(A)” in the table shows a condition in which tetramethylsilane is used as standard substance in chloroform-d solvent and measurement is carried out at 300 MHz (CDCl₃, Me₄Si, 300 MHz), hereinafter, the indication “(B)” shows the measurement condition of (CDCl₃, Me₄Si, 400 MHz), the indication of “(C)” shows the measurement condition of (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz), and the indication of “(D)” shows the measurement condition of (CDCl₃-DMSO-d₆, Me₄Si, 400 MHz).

TABLE 21 No. ¹H NMR 3-010 (A) δ 8.55-8.6 (m, 1H), 7.15-8.05 (m, 15H), 6.95-7.1 (m, 1H), 5.20 (s, 2H), 4.76 (d, J = 4.4 Hz, 2H), 4.10 (d, J = 17.2 Hz, 1H), 3.78 (d, J = 17.2 Hz, 1H). 3-034 (A) δ 7.2-7.5 (m, 7H), 4.55-4.7 (m, 2H), 4.06 (d, J = 17.1 Hz, 1H), 3.67 (d, J = 17.1 Hz, 1H), 2.38 (s, 3H). 3-059 (B) δ 7.9-7.95 (m, 2H), 7.8-7.9 (m, 1H), 7.7-7.8 (m, 2H), 7.51 (s, 2H), 7.4-7.45 (m, 1H), 5.02 (d, J = 7.0 Hz, 2H), 4.12 (d, J = 17.0 Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H). 3-064 (A) δ 7.84 (d, J = 8.4 Hz, 2H), 7.74 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.43 (bs, 1H), 6.42 (bs, 1H), 4.63 (t, J = 5.1 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.65-3.85 (m, 3H), 3.5-3.65 (m, 4H), 1.24 (t, J = 6.8 Hz, 6H). 3-067 (A) δ 7.6-7.8 (m, 3H), 7.54 (d, J = 7.8 Hz, 2H), 7.44 (bs, 2H), 7.38 (bs, 1H), 3.4-4.25 (m, 7H), 4.04 (d, J = 17.7 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H). 3-069 (A) δ 7.82 (d, J = 8.7 Hz, 2H), 7.71 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H), 7.42 (bs, 1H), 6.71 (bs, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.6-3.95 (m, 4H), 3.74 (d, J = 17.1 Hz, 1H), 3.48 (t, J = 6.3 Hz, 2H), 2.55-2.7 (m, 1H), 2.0-2.15 (m, 1H), 1.6-1.75 (m, 1H). 3-072 (A) δ 7.85 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.4-7.5 (m, 1H), 6.44 (bs, 1H), 4.75 (t, J = 4.8 Hz, 1H), 4.1-4.2 (m, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.75-3.9 and 3.6-3.65 (m, 2H), 3.72 (d, J = 17.4 Hz, 1H), 3.6-3.65 (m, 2H), 2.0-2.15 (m, 1H), 1.35-1.45 (m, 1H). 3-074 (A) δ 7.82 (d, J = 8.4 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.4-7.45 (m, 1H), 6.53 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.72 (s, 2H), 3.71 (d, J = 17.4 Hz, 1H), 2.92 (s, 3H), 1.72 (s, 6H). 3-077 (A) δ 9.79 (s, 1H), 7.89 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 7.61 (bs, 2H), 7.51 (bs, 1H), 6.91 (bs, 1H), 4.46 (d, J = 4.5 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H). 3-078 (A) δ 9.27 (bs, 1H), 7.85 (d, J = 8.5 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 7.60 and 6.93 (t, J = 4.4 Hz, 1H), 7.51 (bs, 2H), 7.44 (bs, 1H), 6.71 (bs, 1H), 4.37 and 4.26 (d, J = 4.7 Hz, 2H), 4.11 (d, J = 16.8 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H). 3-079 (A) δ 7.8-7.9 (m, 2H), 7.7-7.8 (m, 2H), 7.45-7.55 (m, 2H), 7.45-7.55 and 6.82 (t, J = 4.4 Hz, 1H), 7.43 (t, J = 2.0 Hz, 1H), 6.71 and 6.60 (bs, 1H), 4.31 and 4.24 (t, J = 4.5 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.94 and 3.88 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H). 3-082 (A) δ 7.90 (d, J = 8.7 Hz, 2H), 7.73 (d, J = 8.7 Hz, 2H), 7.52 (s, 2H), 7.43 (s, 1H), 7.10 (t, J = 4.8 Hz, 1H), 4.21 (d, J = 4.8 Hz, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 3-083 (A) δ 7.87 (d, J = 8.1 Hz, 2H), 7.74 (d, J = 8.1 Hz, 2H), 7.52 (s, 2H), 7.43 (s, 1H), 6.73 (bs, 1H), 4.26 (d, J = 5.1 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.82 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H). 3-087 (A) δ 8.52 (bs, 1H), 7.97 (bs, 1H), 7.88 (d, J = 8.4 Hz, 2H), 7.7-7.8 (m, 3H), 7.51 (s, 2H), 7.43 (s, 1H), 4.45 (d, J = 4.8 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 3-089 (A) δ 7.84 (d, J = 8.5 Hz, 2H), 7.73 (d, J = 8.5 Hz, 2H), 7.51 (bs, 2H), 7.43 (bs, 1H), 6.18 (bs, 1H), 5.85-6.05 (m, 1H), 5.2-5.35 (m, 2H), 4.05-4.15 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H). 3-107 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.55 (s, 1H), 7.51 (bs, 2H), 7.43 (bs, 1H), 6.27 (bs, 1H), 4.48 (d, J = 5.1 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.79 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H). 3-108 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.4-7.45 (m, 1H), 6.34 (bs, 1H), 4.48 (d, J = 5.4 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.81 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H). 3-110 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H), 7.43 (bs, 1H), 6.36 (bs, 1H), 6.17 (s, 1H), 4.65 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.85 (s, 3H), 3.69 (d, J = 17.4 Hz, 1H). 3-114 (A) δ 7.86 (d, J = 8.1 Hz, 2H), 7.71 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.4-7.45 (m, 2H), 7.08 (s, 1H), 6.98 (bs, 1H), 4.68 (d, J = 5.4 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.72 (s, 3H). 3-118 (D) δ 7.95-8.0 (m, 2H), 7.75-7.8 (m, 2H), 7.35-7.55 (m, 4H), 5.45-5.5 (m, 2H), 4.15-4.2 (m, 1H), 3.8-3.85 (m, 1H), 2.57 (s, 3H). 3-119 (B) δ 8.55-8.65 (m, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.65 (d, J = 8.2 Hz, 2H), 7.50 (s, 2H), 7.42 (s, 1H), 6.91 (s, 1H), 6.86 (s, 1H), 4.67 (d, J = 5.3 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.77 (s, 3H), 3.70 (d, J = 17.0 Hz, 1H). 3-120 (B) δ 7.35-8.0 (m, 8H), 6.95 (m, 2H), 6.6-6.75 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.63 (s, 3H). 3-121 (B) δ 8.1-8.2 (m, 1H), 7.65-7.9 (m, 3H), 7.4-7.6 (m, 3H), 7.1-7.2 (m, 1H), 4.86 (d, J = 5.8 Hz, 2H), 4.05-4.15 (m, 1H), 3.65-3.8 (m, 1H), 2.72 (s, 3H). 3-122 (A) δ 8.43 (s, 1H), 7.88 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.1 Hz, 2H), 7.51 (s, 2H), 7.44 (s, 1H), 7.30 (t, J = 5.4 Hz, 1H), 4.93 (d, J = 5.4 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H). 3-127 (B) δ 7.93 (d, J = 8.2 Hz, 2H), 7.82 (t, J = 4.8 Hz, 1H), 7.74 (d, J = 8.2 Hz, 2H), 7.58 (t, J = 7.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.43 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 7.7 Hz, 1H), 7.09 (d, J = 7.7 Hz, 1H), 4.71 (d, J = 4.8 Hz, 2H), 3.93 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.57 (s, 3H). 3-131 (A) δ 8.55 (s, 1H), 8.40 (s, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.72 (d, J = 8.2 Hz, 2H), 7.53 (s, 3H), 7.42 (s, 1H), 4.7-4.8 (m, 2H), 4.13 (d, J = 17.0 Hz, 1H), 3.74 (d, J = 17.0 Hz, 1H), 2.57 (s, 3H). 3-134 (A) δ 9.64 (bs, 1H), 7.81 (d, J = 8.1 Hz, 2H), 7.69 (d, J = 8.1 Hz, 2H), 7.50 (s, 2H), 7.43 (s, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.86 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H). 3-135 (A) δ 8.19 (d, J = 4.2 Hz, 1H), 7.95 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 7.5-7.6 (m, 4H), 7.44 (s, 1H), 7.10 (bs, 1H), 6.84 (t, J = 8.4 Hz, 1H), 6.78 (d, J = 8.4 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H). 3-143 (A) δ 8.57 (d, J = 5.1 Hz, 1H), 8.21 (bs, 1H), 7.85-8.05 (m, 2H), 7.6-7.8 (m, 3H), 7.15-7.45 (m, 5H), 4.72 (d, J = 5.1 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H), 2.38 (s, 3H). 3-147 (A) δ 7.86 (d, J = 8.5 Hz, 2H), 7.77 (d, J = 8.5 Hz, 2H), 7.55-7.65 (m, 1H), 7.2-7.3 (m, 1H), 4.05-4.25 (m, 3H), 3.86 (d, J = 17.0 Hz, 1H), 2.30 (s, 3H). 4-003 (A) δ 8.5-8.7 (m, 1H), 7.35-7.9 (m, 9H), 7.1-7.3 (m, 1H), 4.5-5.1 (m, 4H), 4.0-4.2 (m, 1H), 3.6-3.8 (m, 1H), 3.15-3.55 (m, 3H). 4-004 (A) δ 8.55-8.65 (m, 1H), 7.35-7.8 (m, 9H), 7.1-7.3 (m, 1H), 4.6-5.15 (m, 4H), 3.3-4.2 (m, 4H), 1.1-1.35 (m, 3H). 4-005 (A) δ 8.2-8.3 (m, 1H), 7.15-7.8 (m, 10H), 4.75-5.35 (m, 4H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.04 and 2.84 (bs, 3H). 4-006 (B) δ 8.5-8.6 (m, 1H), 7.1-7.75 (m, 10H), 5.65-5.95 (m, 1H), 5.1-5.3 (m, 2H), 4.85 and 4.53 (s, 2H), 3.6-4.2 (m, 4H). 4-007 (B) δ 8.5-8.7 (m, 1H), 6.95-7.75 (m, 10H), 5.65-6.1 (m, 2H), 5.1-5.45 (m, 4H), 4.4-4.9 (m, 4H), 3.75-4.2 (m, 3H). 4-008 (A) δ 8.50 (bs, 1H), 7.0-7.75 (m, 15H), 4.35-4.9 (m, 4H), 4.05 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H). 4-009 (A) δ 8.5-8.55 (m, 1H), 7.65-7.75 (m, 5H), 7.51 (s, 2H), 7.42 (s, 1H), 7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.17 (s, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 3.60 (s, 3H). 4-010 (A) δ 8.37 (bs, 1H), 7.65-7.8 (m, 3H), 7.3-7.55 (m, 6H), 4.4-4.9 (m, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.1-3.65 (m, 2H), 1.12 (bs, 3H). 4-011 (B) δ 7.7-7.8 (m, 4H), 7.52 (s, 2H), 7.43 (s, 1H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 3.53 (s, 3H), 3.37 (s, 3H). 5-001 (A) δ 8.51 (d, J = 4.8 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.62 (s, 1H), 7.45-7.55 (m, 2H), 7.25-7.4 (m, 4H), 7.22 (dd, J = 6.9, 2.5 Hz, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 16.8 Hz, 1H), 3.73 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H). 5-003 (A) δ 8.51 (d, J = 4.8 Hz, 1H), 7.77 (s, 1H), 7.68 (t, J = 4.5 Hz, 1H), 7.45-7.6 (m, 5H), 7.25-7.35 (m, 3H), 7.22 (dd, J = 7.5, 1.8 Hz, 1H), 4.73 (d, J = 4.5 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-007 (A) δ 8.52 (d, J = 4.2 Hz, 1H), 7.78 (d, J = 9.3 Hz, 2H), 7.67 (t, J = 5.1 Hz, 1H), 7.51 (bs, 3H), 7.3-7.4 (m, 4H), 7.15-7.25 (m, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-009 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.89 (bs, 1H), 7.82 (d, J = 7.8 Hz, 1H), 7.65-7.75 (m, 2H), 7.60 (t, J = 7.8 Hz, 1H), 7.5-7.55 (m, 3H), 7.33 (bs, 1H), 7.32 (d, J = 7.8 Hz, 1H), 7.21 (dd, J = 7.2, 1.5 Hz, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.15 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-010 (A) δ 7.25-7.6 (m, 7H), 6.37 (bs, 1H), 4.0-4.15 (m, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.77 and 3.75 (d, J = 17.4 Hz, 1H), 2.95 (dd, J = 10.2, 8.7 Hz, 1H), 2.41 (s, 3H), 2.03 (dd, J = 10.2, 3.3 Hz, 1H), 1.90 (dd, J = 8.7, 3.3 Hz, 1H). 5-011 (A) δ 8.51 (d, J = 4.2 Hz, 1H), 7.69 (t, J = 4.8 Hz, 1H), 7.15-7.6 (m, 10H), 4.72 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.77 (dd, J = 17.1, 3.0 Hz, 1H), 2.95 (dd, J = 10.2, 8.4 Hz, 1H), 2.48 (s, 3H), 2.02 (dd, J = 10.2, 3.0 Hz, 1H), 1.89 (dd, J = 8.4, 3.0 Hz, 1H). 5-012 (A) δ 7.25-7.5 (m, 7H), 7.16 (bs, 1H), 4.0-4.2 (m, 3H), 3.75 (d, J = 17.2 Hz, 1H), 2.42 (s, 3H). 5-013 (A) δ 8.5-8.6 (m, 1H), 7.65-7.8 (m, 1H), 7.15-7.6 (m, 10H), 4.72 (d, J = 5.2 Hz, 2H), 4.12 (d, J = 17.3 Hz, 1H), 3.74 (d, J = 17.3 Hz, 1H), 2.46 (s, 3H). 5-015 (B) δ 8.5-8.55 (m, 1H), 7.72 (td, J = 6.8, 4.8 Hz, 1H), 7.45-7.6 (m, 5H), 7.2-7.4 (m, 5H), 4.75 (d, J = 4.8 Hz, 2H), 4.11 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H). 5-016 (A) δ 7.35-7.6 (m, 6H), 7.2-7.3 (m, 1H), 6.10 (d, J = 53.4 Hz, 1H), 6.06 (bs, 1H), 4.0-4.2 (m, 3H), 3.72 (d, J = 16.8 Hz, 1H), 2.47 (s, 3H). 5-017 (A) δ 8.54 (d, J = 4.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.35-7.6 (m, 6H), 7.2-7.35 (m, 4H), 6.10 (d, J = 53.1 Hz, 1H), 4.75 (d, J = 5.1 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-018 (A) δ 8.45-8.55 (m, 1H), 7.15-7.75 (m, 14H), 6.95-7.05 (m, 1H), 5.19 (s, 2H), 4.74 (d, J = 4.4 Hz, 2H), 4.07 (d, J = 16.8 Hz, 1H), 3.75 (d, J = 16.8 Hz, 1H), 2.49 (s, 3H). 5-019 (A) δ 8.24 (s, 1H), 8.00 (s, 1H), 7.2-7.6 (m, 6H), 7.2-7.3 (m, 1H), 6.44 (t, J = 6.5 Hz, 1H), 3.95-4.15 (m, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.78 (d, J = 17.1 Hz, 1H), 2.40 (s, 3H). 5-020 (A) δ 8.52 (d, J = 4.8 Hz, 1H), 8.25 (s, 1H), 8.00 (s, 1H), 7.45-7.75 (m, 7H), 7.15-7.35 (m, 4H), 4.74 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.78 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-021 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.25-7.4 (m, 5H), 7.21 (dd, J = 7.2, 1.5 Hz, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.98 (q, J = 7.2 Hz, 2H), 2.48 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H). 5-022 (A) δ 7.89 (s, 1H), 7.7-7.8 (m, 2H), 7.5-7.6 (m, 3H), 7.45 (d, J = 8.0 Hz, 1H), 6.06 (t, J = 6.2 Hz, 1H), 4.0-4.2 (m, 3H), 3.73 (d, J = 16.6 Hz, 1H), 2.47 (s, 3H). 5-023 (A) δ 8.55 (d, J = 4.7 Hz, 1H), 7.90 (s, 1H), 7.65-7.8 (m, 3H), 7.5-7.6 (m, 4H), 7.3-7.45 (m, 2H), 7.2-7.3 (m, 1H), 4.74 (d, J = 5.0 Hz, 2H), 4.12 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H). 5-024 (B) δ 7.65 (d, J = 8.1 Hz, 1H), 7.45-7.6 (m, 4H), 7.40 (d, J = 7.9 Hz, 1H), 7.34 (d, J = 7.7 Hz, 1H), 6.35 (bs, 1H), 4.0-4.15 (m, 3H), 3.73 (d, J = 17.2 Hz, 1H), 3.37 (s, 3H), 2.43 (s, 3H). 5-025 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.7, 1.6 Hz, 1H), 7.3-7.7 (m, 7H), 7.28 (d, J = 4.6 Hz, 1H), 7.26 (t, J = 4.8 Hz, 1H), 7.23 (dd, J = 7.5, 5.9 Hz, 1H), 4.75 (d, J = 4.8 Hz, 2H), 4.12 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 3.39 (s, 3H), 2.50 (s, 3H). 5-026 (B) δ 7.4-7.65 (m, 6H), 7.36 (d, J = 7.9 Hz, 1H), 6.34 (t, J = 6.1 Hz, 1H), 4.11 (d, J = 17.2 Hz, 1H), 4.08 (qd, J = 9.6, 6.6 Hz, 2H), 3.73 (d, J = 17.4 Hz, 1H), 3.50 (d, J = 0.9 Hz, 3H), 2.41 (s, 3H). 5-027 (B) δ 8.53 (ddd, J = 4.9, 1.6, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H), 7.6-7.65 (m, 2H), 7.5-7.55 (m, 4H), 7.44 (ddd, J = 7.9, 2.0, 1.3 Hz, 1H), 7.33 (d, J = 7.7 Hz, 1H), 7.26 (t, J = 4.8 Hz, 1H), 7.22 (ddd, J = 7.5, 4.8, 1.1 Hz, 1H), 4.75 (d, J = 4.8 Hz, 2H), 4.12 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 3.51 (s, 3H), 2.49 (s, 3H). 5-028 (B) δ 8.5-8.55 (m, 1H), 7.83 (bs, 1H), 7.2-7.75 (m, 15H), 4.76 (d, J = 4.8 Hz, 2H), 4.13 (dd, J = 17.2, 1.8 Hz, 1H), 3.82 (d, J = 17.2 Hz, 1H), 2.51 (s, 3H). 5-029 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.51 (bs, 2H), 7.50 (bs, 1H), 7.15-7.4 (m, 5H), 6.8-6.95 (m, 1H), 4.74 (d, J = 4.8 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-030 (A) δ 7.2-7.45 (m, 6H), 6.49 (bs, 1H), 4.0-4.15 (m, 2H), 3.46 (s, 2H), 2.40 (s, 3H), 1.79 (s, 3H). 5-031 (A) δ 7.25-7.5 (m, 6H), 6.50 (bs, 1H), 4.0-4.15 (m, 2H), 3.60 (d, J = 16.8 Hz, 1H), 3.39 (d, J = 16.8 Hz, 1H), 2.38 (s, 3H), 2.15-2.3 (m, 1H), 0.98 (d, J = 6.6 Hz, 3H), 0.90 (d, J = 6.9 Hz, 3H). 5-033 (A) δ 8.51 (d, J = 4.8 Hz, 1H), 7.69 (t, J = 4.5 Hz, 1H), 7.45-7.5 (m, 3H), 7.41 (bs, 2H), 7.15-7.4 (m, 4H), 4.73 (d, J = 4.5 Hz, 2H), 3.57 (d, J = 16.8 Hz, 1H), 3.47 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.35-1.5 (m, 1H), 0.45-0.7 (m, 4H). 5-035 (B) δ 8.5-8.55 (m, 1H), 7.72 (td, J = 7.6, 1.8 Hz, 1H), 7.5-7.55 (m, 4H), 7.43 (d, J = 1.8 Hz, 2H), 7.35-7.4 (m, 2H), 7.2-7.25 (m, 1H), 4.76 (d, J = 4.8 Hz, 2H), 3.93 (d, J = 16.8 Hz, 1H), 3.85 (dd, J = 18.6, 11.8 Hz, 2H), 3.53 (d, J = 16.8 Hz, 1H), 2.50 (s, 3H). 5-037 (A) δ 8.53 (d, J = 5.0 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.6 (m, 9H), 5.89 (t, J = 55.2 Hz, 1H), 4.74 (d, J = 4.7 Hz, 2H), 4.00 (d, J = 17.0 Hz, 1H), 3.55 (d, J = 17.0 Hz, 1H), 2.50 (s, 3H). 5-038 (B) δ 8.17 (t, J = 7.0 Hz, 1H), 7.45-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.0-7.1 (m, 1H), 4.05-4.25 (m, 3H), 3.73 (d, J = 17.4 Hz, 1H). 5-040 (A) δ 8.82 (s, 1H), 8.19 (t, J = 7.8 Hz, 1H), 7.4-7.6 (m, 6H), 7.31 (s, 1H), 4.84 (d, J = 5.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H). 5-042 (B) δ 8.03 (m, 1H), 7.64 (d, J = 1.1 Hz, 1H), 7.58 (d, J = 0.8 Hz, 1H), 7.50 (s, 2H), 7.43 (bs, 1H), 6.39 (bs, 1H), 4.18 (d, J = 16.0 Hz, 1H), 4.1-4.2 (m, 2H), 3.80 (d, J = 16.0 Hz, 1H). 5-048 (A) δ 8.22 (d, J = 8.7 Hz, 2H), 7.81 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 1.2 Hz, 1H), 7.63 (dd, J = 8.4, 1.8 Hz, 1H), 7.54 (d, J = 8.7 Hz, 2H), 7.50 (bs, 2H), 7.44 (d, J = 2.1 Hz, 1H), 6.72 (bs, 1H), 4.77 (d, J = 6.3 Hz, 2H), 4.04 (d, J = 17.1 Hz, 1H), 3.66 (d, J = 17.1 Hz, 1H). 5-049 (A) δ 7.81 (d, J = 8.1 Hz, 1H), 7.7-7.75 (m, 2H), 7.63 (dd, J = 8.1, 1.8 Hz, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.34 (d, J = 3.3 Hz, 1H), 7.16 (bs, 1H), 5.00 (d, J = 5.4 Hz, 2H), 4.06 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H). 5-050 (A) δ 8.79 (s, 1H), 7.75 (dd, J = 8.4, 3.0 Hz, 1H), 7.70 (bs, 1H), 7.60 (bs, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.33 (s, 1H), 7.01 (bs, 1H), 4.82 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H). 5-051 (A) δ 7.7-7.8 (m, 2H), 7.61 (dd, J = 8.1, 1.5 Hz, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.19 (s, 1H), 6.84 (bs, 1H), 4.69 (d, J = 5.7 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H). 5-052 (B) δ 8.63 (s, 1H), 7.25-7.75 (m, 7H), 5.10 (d, J = 5.8 Hz, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H). 5-053 (A) δ 8.54 (d, J = 4.2 Hz, 1H), 7.77 (d, J = 7.8 Hz, 1H), 7.6-7.8 (m, 3H), 7.62 (d, J = 7.8 Hz, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.34 (d, J = 7.5 Hz, 1H), 7.23 (dd, J = 7.5, 2.4 Hz, 1H), 4.78 (d, J = 4.5 Hz, 2H), 4.08 (d, J = 18.0 Hz, 1H), 3.71 (d, J = 18.0 Hz, 1H). 5-056 (A) δ 8.55 (d, J = 4.5 Hz, 1H), 8.08 (t, J = 4.5 Hz, 1H), 7.96 (s, 1H), 7.78 (d, J = 8.4 Hz, 1H), 7.72 (d, J = 8.4 Hz, 1H), 7.69 (dd, J = 4.5, 2.4 Hz, 1H), 7.50 (bs, 2H), 7.43 (bs, 1H), 7.33 (d, J = 7.2 Hz, 1H), 7.23 (dd, J = 7.2, 2.4 Hz, 1H), 4.73 (d, J = 4.5 Hz, 2H), 4.28 (d, J = 18.0 Hz, 1H), 3.87 (d, J = 18.0 Hz, 1H). 5-058 (B) δ 8.54 (d, J = 3.9 Hz, 1H), 7.89 (bs, 1H), 7.74 (td, J = 7.8, 1.8 Hz, 1H), 7.6-7.7 (m, 1H), 7.50 (bs, 3H), 7.44 (t, J = 1.8 Hz, 1H), 7.38 (d, J = 7.8 Hz, 1H), 7.2-7.3 (bs, 1H), 4.79 (d, J = 4.7 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H). 5-060 (B) δ 8.01 (bs, 1H), 7.65-7.75 (m, 2H), 7.50 (bs, 2H), 7.4-7.45 (m, 1H), 6.25-6.3 (m, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.55-3.75 (m, 3H), 3.45-3.6 (m, 4H), 1.20 (t, J = 7.0 Hz, 3H). 5-061 (B) δ 8.10 (bs, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.50 (bs, 2H), 7.4-7.45 (m, 2H), 6.09 (bs, 1H), 4.54 (t, J = 5.2 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.60 (t, J = 5.2 Hz, 2H), 3.44 (s, 6H). 5-062 (B) δ 8.13 (bs, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.4-7.5 (m, 4H), 6.7-6.9 (br, 1H), 6.05-6.3 (br, 1H), 4.05-4.15 (m, 2H), 4.06 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.88 (bs, 3H). 5-065 (B) δ 8.5-8.55 (m, 1H), 8.13 (d, J = 1.8 Hz, 1H), 7.7-7.5 (m, 2H), 7.50 (d, J = 1.8 Hz, 2H), 7.44 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 8.0 Hz, 1H), 7.2-7.3 (m, 3H), 4.78 (d, J = 4.8 Hz, 2H), 4.06 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H). 5-070 (A) δ 7.35-7.55 (m, 6H), 6.02 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.25-3.35 (m, 2H), 2.45 (s, 3H), 1.0-1.15 (m, 1H), 0.55-0.65 (m, 2H), 0.25-0.35 (m, 2H). 5-072 (A) δ 7.35-7.55 (m, 6H), 5.78 (bs, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 3.47 (t, J = 7.1 Hz, 2H), 2.45-2.65 (m, 1H), 2.44 (s, 3H), 1.65-2.2 (m, 6H). 5-077 (A) δ 7.4-7.5 (m, 6H), 6.19 (bs, 1H), 4.08 (d, J = 16.8 Hz, 1H), 3.5-3.75 (m, 7H), 2.47 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H). 5-079 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 6.28 (bs, 1H), 4.27 (t, J = 5.1 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 3H), 2.44 (s, 3H), 2.08 (s, 3H). 5-080 (B) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.48 (bs, 1H), 4.80 (bs, 1H), 4.28 (t, J = 5.0 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.65-3.7 (m, 2H), 3.15-3.25 (m, 2H), 2.46 (s, 3H), 1.13 (t, J = 7.2 Hz, 3H). 5-083 (A) δ 7.4-7.55 (m, 6H), 5.95 (bs, 1H), 4.48 (t, J = 5.4 Hz, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H), 3.59 (t, J = 5.4 Hz, 2H), 3.44 (s, 6H), 2.48 (s, 3H). 5-084 (A) δ 7.4-7.55 (m, 6H), 6.02 (bs, 1H), 4.63 (t, J = 5.1 Hz, 1H), 4.08 (d, J = 16.8 Hz, 1H), 3.5-3.8 (m, 7H), 2.48 (s, 3H), 1.22 (t, J = 6.6 Hz, 6H). 5-085 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 6.31 (d, J = 8.1 Hz, 1H), 4.81 (bs, 1H), 4.35-4.45 (m, 1H), 4.22 (dd, J = 11.5, 6.8 Hz, 1H), 4.10 (dd, J = 11.5, 3.7 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.15-3.25 (m, 2H), 2.45 (s, 3H), 1.27 (d, J = 7.1 Hz, 3H), 1.13 (t, J = 7.2 Hz, 3H). 5-086 (A) δ 7.35-7.6 (m, 6H), 6.24 (bs, 1H), 4.0-4.15 (m, 2H), 3.65-3.9 (m, 4H) 3.25-3.35 (m, 1H), 2.46 (s, 3H), 1.85-2.1 (m, 3H), 1.55-1.7 (m, 1H). 5-087 (A) δ 7.35-7.55 (m, 6H), 5.97 (bs, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.55-4.0 (m, 4H), 3.69 (d, J = 17.1 Hz, 1H), 3.45-3.5 (m, 2H), 2.55-2.65 (m, 1H), 2.47 (s, 3H), 2.05-2.15 (m, 1H), 1.6-1.75 (m, 1H). 5-090 (A) δ 7.4-7.55 (m, 6H), 6.14 (bs, 1H), 4.75 (t, J = 4.5 Hz, 1H), 4.1-4.2 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.75-3.9 (m, 2H), 3.71 (d, J = 17.4 Hz, 1H), 3.5-3.65 (m, 2H), 2.47 (s, 3H), 2.0-2.15 (m, 1H), 1.3-1.45 (m, 1H). 5-092 (A) δ 7.35-7.6 (m, 6H), 7.05 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.9-4.05 (m, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.1-3.25 (m, 1H), 2.8-2.95 (m, 1H), 2.66 (s, 3H), 2.47 (s, 3H). 5-094 (A) δ 7.4-7.6 (m, 6H), 6.73 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.9-4.05 (m, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.28 (t, J = 5.7 Hz, 2H), 3.08 (q, J = 7.5 Hz, 2H), 2.47 (s, 3H), 1.43 (t, J = 7.5 Hz, 3H). 5-095 (A) δ 7.2-7.6 (m, 11H), 6.09 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.75 (s, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.5-3.6 (m, 2H), 2.68 (t, J = 6.3 Hz, 2H), 2.45 (s, 3H). 5-096 (A) δ 7.35-7.55 (m, 11H), 6.62 (t, J = 6.0 Hz, 1H), 4.30 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H), 3.1-3.2 (m, 2H), 2.41 (s, 3H). 5-097 (A) δ 7.35-7.55 (m, 6H), 7.32 (s, 1H), 6.30 (bs, 1H), 6.22 (d, J = 2.7 Hz, 1H), 6.13 (bs, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.77 (s, 2H), 3.70 (d, J = 17.4 Hz, 1H), 3.55-3.65 (m, 2H), 2.78 (t, J = 6.3 Hz, 2H), 2.47 (s, 3H). 5-098 (A) δ 7.4-7.55 (m, 7H), 6.55-6.6 (m, 2H), 6.45 (dd, J = 3.0, 1.8 Hz, 1H), 4.39 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H), 3.25-3.3 (m, 2H), 2.45 (s, 3H). 5-099 (A) δ 7.4-7.6 (m, 6H), 6.22 (t, J = 5.4 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.6-3.75 (m, 2H), 3.35-3.5 (m, 1H), 2.85-3.05 (m, 1H), 2.49 (s, 3H), 2.11 (s, 3H), 1.35 (d, J = 6.9 Hz, 3H). 5-100 (A) δ 7.4-7.6 (m, 6H), 7.15-7.25 and 6.9-7.0 (m, 1H), 3.9-4.2 (m, 2H), 3.6-3.85 (m, 2H), 2.85-3.2 (m, 1H), 2.68 and 2.56 (s, 3H), 2.49 (s, 3H), 1.32 (d, J = 6.9 Hz, 3H). 5-101 (A) δ 7.4-7.6 (m, 6H), 6.65 (t, J = 5.8 Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.75-4.0 (m, 2H), 3.69 (d, J = 17.3 Hz, 1H), 3.25-3.45 (m, 1H), 2.94 (s, 3H), 2.49 (s, 3H), 1.50 (d, J = 6.9 Hz, 3H). 5-102 (A) δ 7.35-7.65 (m, 6H), 6.08 (bs, 1H), 4.3-4.45 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.71 (d, J = 5.7 Hz, 2H), 2.44 (s, 3H), 2.17 (s, 3H), 1.34 (d, J = 6.6 Hz, 3H). 5-103 (A) δ 7.4-7.6 (m, 6H), 6.46 (d, J = 8.1 Hz, 1H), 4.6-4.75 (m, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.42 (dd, J = 14.4, 6.3 Hz, 1H), 3.26 (dd, J = 14.4, 5.1 Hz, 1H), 3.03 (s, 3H), 2.45 (s, 3H), 1.53 (d, J = 6.9 Hz, 3H). 5-104 (A) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H), 5.75 (bs, 1H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 3.07 (s, 2H), 2.48 (s, 3H), 2.18 (s, 3H), 1.51 (s, 6H). 5-112 (A) δ 7.45-7.65 (m, 6H), 7.43 and 6.93 (t, J = 4.8 Hz, 1H), 6.29 (bs, 1H), 4.33 and 4.25 (t, J = 4.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-114 (A) δ 7.4-7.6 (m, 6H), 7.43 and 6.85 (bs, 1H), 6.30 (bs, 1H), 4.25-4.35 and 4.2-4.25 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.93 and 3.86 (d, J = 7.2 Hz, 2H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H), 1.1-1.3 (m, 1H), 0.5-0.6 (m, 2H), 0.2-0.3 (m, 2H). 5-115 (A) δ 7.57 and 6.86 (t, J = 4.4 Hz, 1H), 7.25-7.55 (m, 10H), 6.26 (bs, 1H), 5.10 and 5.02 (s, 2H), 4.28 and 4.20 (t, J = 5.3 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.44 (s, 3H). 5-116 (A) δ 7.4-7.5 (m, 6H), 7.39 and 6.79 (t, J = 4.5 Hz, 1H), 6.25 and 6.15 (bs, 1H), 4.0-4.3 (m, 4H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.46 and 2.45 (s, 3H), 0.9-1.25 (m, 2H), 0.01 (s, 9H). 5-118 (A) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.19 (bs, 1H), 4.7-4.85 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.7-3.8 (m, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.5-3.6 (m, 1H), 3.0-3.15 (m, 1H), 2.7-2.85 (m, 1H), 2.47 (s, 3H), 2.00 (s, 3H). 5-120 (A) δ 7.4-7.6 (m, 6H), 7.11 (d, J = 9.6 Hz, 1H), 6.30 (d, J = 9.6 Hz, 1H), 4.0-4.25 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 2.50 (s, 3H). 5-122 (A) δ 7.4-7.6 (m, 7H), 6.61 (d, J = 3.3 Hz, 1H), 6.49 (d, J = 8.4 Hz, 1H), 6.44 (dd, J = 3.3, 2.1 Hz, 1H), 6.33 (d, J = 8.4 Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.48 (s, 3H). 5-123 (A) δ 7.3-7.6 (m, 8H), 7.0-7.1 (m, 1H), 6.49 (d, J = 8.8 Hz, 1H), 6.42 (d, J = 8.8 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 2.50 (s, 3H). 5-126 (A) δ 8.62 (d, J = 5.0 Hz, 1H), 7.85 (td, J = 8.1, 2.1 Hz, 1H), 7.35-7.65 (m, 9H), 6.15 (d, J = 6.9 Hz, 1H), 4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.52 (s, 3H). 5-128 (A) δ 7.45-7.65 (m, 6H), 6.33 (bs, 1H), 4.23 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.81 (s, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-130 (B) δ 7.4-7.55 (m, 6H), 6.33 (d, J = 6.6 Hz, 1H), 4.75-4.85 (m, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.81 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H), 1.55 (s, 3H). 5-131 (B) δ 7.4-7.55 (m, 6H), 6.34 (d, J = 7.6 Hz, 1H), 4.7-4.8 (m, 1H), 4.2-4.3 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H), 1.54 (t, J = 7.0 Hz, 3H), 1.32 (t, J = 7.2 Hz, 3H). 5-132 (A) δ 7.4-7.55 (m, 6H), 6.36 (bs, 1H), 4.75-4.9 (m, 1H), 4.6-4.75 (m, 1H), 4.4-4.55 (m, 1H), 4.18 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H). 5-133 (A) δ 7.4-7.6 (m, 6H), 7.06 (d, J = 6.6 Hz, 1H), 5.76 (t, J = 6.6 Hz, 1H), 4.27 (d, J = 6.6 Hz, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.89 (s, 3H), 3.70 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H). 5-134 (A) δ 7.4-7.6 (m, 6H), 6.79 (d, J = 9.4 Hz, 1H), 5.72 (d, J = 9.4 Hz, 1H), 4.09 (d, J = 17.3 Hz, 1H), 3.87 (s, 3H), 3.71 (d, J = 17.3 Hz, 1H), 3.59 (s, 3H), 2.51 (s, 3H). 5-136 (A) δ 7.35-7.55 (m, 6H), 6.44 (bs, 1H), 4.05-4.25 (m, 3H), 3.6-3.8 (m, 3H), 2.66 (t, J = 6.0 Hz, 2H), 2.46 (s, 3H), 1.27 (t, J = 7.2 Hz, 3H). 5-138 (A) δ 7.45-7.6 (m, 6H), 7.09 (bs, 1H), 6.69 (bs, 1H), 4.05-4.15 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H), 2.83 (d, J = 4.8 Hz, 3H), 2.44 (s, 3H). 5-139 (A) δ 7.5-7.6 (m, 5H), 7.43 (s, 1H), 6.98 (bs, 1H), 4.23 (d, J = 3.9 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 3.04 (s, 3H), 3.02 (s, 3H), 2.50 (s, 3H). 5-141 (B) δ 7.4-7.55 (m, 6H), 7.05-7.1 (m, 1H), 6.62 (bs, 1H), 4.05-4.15 (m, 3H), 3.72 (d, J = 17.2 Hz, 1H), 3.23 (dd, J = 13.8, 7.2 Hz, 2H), 2.45 (s, 3H), 1.5-1.6 (m, 2H), 0.91 (t, J = 7.4 Hz, 3H). 5-143 (B) δ 7.4-7.55 (m, 6H), 6.9-7.05 (m, 1H), 6.45-6.55 (m, 1H), 4.05-4.2 (m, 3H), 3.70 (d, J = 17.2 Hz, 1H), 3.1-3.15 (m, 2H), 2.45-2.5 (m, 4H), 0.9-1.0 (m, 6H). 5-145 (B) δ 7.4-7.55 (m, 6H), 6.78 (bs, 1H), 5.93 (bs, 1H), 4.0-4.15 (m, 3H), 3.70 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.38 (s, 9H). 5-146 (B) δ 7.4-7.55 (m, 6H), 7.01 (bs, 1H), 6.53 (bs, 1H), 4.05-4.2 (m, 3H), 3.71 (d, J = 17.4 Hz, 1H), 3.05-3.1 (m, 2H), 2.46 (s, 3H), 0.91 (s, 9H). 5-147 (B) δ 7.4-7.55 (m, 6H), 6.89 (bs, 2H), 4.56 (t, J = 5.0 Hz, 1H), 4.44 (t, J = 5.0 Hz, 1H), 4.16 (d, J = 5.0 Hz, 2H), 4.19 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.5-3.7 (m, 2H), 2.46 (s, 3H). 5-149 (A) δ 7.45-7.6 (m, 5H), 7.42 (s, 1H), 7.27 (bs, 1H), 4.25-4.4 (m, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.6-3.8 (m, 5H), 3.17 (s, 3H), 2.49 (s, 3H). 5-150 (B) δ 7.4-7.55 (m, 6H), 6.8-7.2 (m, 2H), 4.16 (d, J = 5.0 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.5-3.75 (m, 3H), 3.48 (t, J = 5.8 Hz, 2H), 2.48 (s, 3H). 5-152 (A) δ 7.4-7.55 (m, 6H), 7.05 (bs, 1H), 6.90 (bs, 1H), 4.0-4.2 (m, 3H), 3.71 (d, J = 17.0 Hz, 1H), 3.5-3.6 (m, 2H), 3.4-3.5 (m, 2H), 2.45 (s, 3H), 1.9-2.1 (m, 2H). 5-153 (B) δ 7.4-7.55 (m, 6H), 6.7-7.05 (m, 2H), 4.15-4.2 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.75-3.9 (m, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.05-3.2 (m, 1H), 2.47 (s, 3H), 1.49 (bs, 1H), 1.6-1.7 (m, 1H), 1.2-1.3 (m, 1H). 5-154 (A) δ 7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.86 (bs, 1H), 6.77 (bs, 1H), 4.05-4.15 (m, 3H), 3.65-3.8 (m, 3H), 3.45-3.55 (m, 2H), 2.46 (s, 3H), 1.69 (bs, 1H). 5-155 (B) δ 7.5-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.9-7.0 (m, 1H), 4.25-4.4 (m, 2H), 4.19 (d, J = 17.4 Hz, 1H), 3.8-3.9 (m, 2H), 3.70 (d, J = 17.4 Hz, 1H), 3.63 (t, J = 5.2 Hz, 1H), 3.49 (t, J = 5.2 Hz, 1H), 3.13 and 3.04 (s, 3H), 2.50 (s, 3H). 5-159 (B) δ 7.4-7.55 (m, 6H), 7.25-7.35 (m, 1H), 7.0-7.05 (m, 1H), 4.10 (d, J = 17.2 Hz, 1H), 4.06 (bs, 2H), 3.77 (bs, 2H), 3.73 (d, J = 17.2 Hz, 1H), 3.25 (t, J = 5.6 Hz, 2H), 2.96 (s, 3H), 2.42 (s, 3H). 5-161 (B) δ 7.4-7.55 (m, 6H), 6.96 (bs, 1H), 5.7-5.85 (m, 1H), 5.15-5.35 (m, 2H), 4.2-4.3 (m, 2H), 4.05-4.15 (m, 2H), 3.92 (bs, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.01 and 2.99 (s, 3H), 2.50 (s, 3H). 5-162 (B) δ 7.45-7.55 (m, 5H), 7.4-7.45 (m, 1H), 6.97 (bs, 1H), 5.7-5.85 (m, 2H), 5.15-5.3 (m, 4H), 4.27 (d, J = 4.0 Hz, 2H), 4.10 (d, J = 17.2 Hz, 1H), 4.05 (d, J = 5.8 Hz, 2H), 3.91 (d, J = 5.8 Hz, 2H), 3.72 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H). 5-163 (A) δ 7.4-7.6 (m, 6H), 6.9-7.2 (m, 2H), 5.38 (s, 1H), 5.30 (s, 1H), 4.0-4.3 (m, 5H), 3.70 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H). 5-165 (B) δ 7.4-7.55 (m, 6H), 7.00 (bs, 2H), 4.05-4.2 (m, 5H), 3.72 (d, J = 17.2 Hz, 1H), 2.54 (s, 3H), 2.22 (s, 1H). 5-167 (B) δ 8.78 (d, J = 1.8 Hz, 1H), 7.45-7.55 (m, 6H), 7.43 (t, J = 1.8 Hz, 1H), 6.65-6.8 (m, 2H), 4.65 (d, J = 7.4 Hz, 2H), 4.05-4.2 (m, 3H), 3.70 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H). 5-168 (B) δ 8.52 (d, J = 4.1 Hz, 1H), 7.67 (td, J = 7.8, 1.8 Hz, 1H), 7.4-7.55 (m, 8H), 7.2-7.25 (m, 1H), 6.83 (bs, 1H), 4.59 (d, J = 5.0 Hz, 2H), 4.22 (d, J = 5.0 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H). 5-171 (B) δ 7.45-7.55 (m, 6H), 6.94 (bs, 1H), 4.25 (d, J = 3.8 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 7H), 3.48 (t, J = 4.4 Hz, 2H), 2.50 (s, 3H). 5-173 (B) δ 7.2-7.6 (m, 7H), 6.6-7.1 (m, 6H), 4.0-4.6 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 3.33 (s, 3H), 2.49 (s, 3H). 5-176 (B) δ 7.3-7.55 (m, 12H), 6.37 (bs, 1H), 5.71 (d, J = 7.0 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.75 (d, J = 4.9 Hz, 3H), 2.41 (s, 3H). 5-178 (A) δ 7.45-7.6 (m, 5H), 7.43 (s, 1H), 6.62 (bs, 1H), 4.37 (t, J = 9.3 Hz, 2H), 4.23 (d, J = 4.5 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.86 (t, J = 9.3 Hz, 2H), 3.71 (d, J = 17.1 Hz, 1H), 2.48 (s, 3H). 5-179 (A) δ 8.10 (bs, 1H), 7.4-7.65 (m, 7H), 7.06 (bs, 1H), 4.43 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H). 5-180 (A) δ 7.65-7.8 (m, 2H), 7.1-7.6 (m, 12H), 6.03 (d, J = 7.4 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 2.45 (s, 3H). 5-181 (A) δ 7.51 (bs, 4H), 7.4-7.45 (m, 1H), 7.38 (d, J = 8.5 Hz, 1H), 5.5-5.6 (m, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.97 (d, J = 6.1 Hz, 2H), 2.46 (s, 3H), 0.13 (s, 9H). 5-182 (A) δ 7.51 (bs, 4H), 7.4-7.45 (m, 2H), 5.85-6.05 (m, 1H), 5.81 (bs, 1H), 5.15-5.35 (m, 2H), 4.05-4.15 (m, 3H), 3.69 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-183 (A) δ 7.4-7.75 (m, 5H), 7.33 (d, J = 7.8 Hz, 1H), 4.04 (d, J = 17.1 Hz, 1H), 3.75 (m, 1H), 3.66 (d, J = 17.4 Hz, 1H), 3.37 (m, 1H), 3.08 (m, 2H), 1.25 (t, J = 7.4 Hz, 3H), 1.04 (t, J = 7.2 Hz, 3H). 5-184 (A) δ 7.51 (bs, 4H), 7.4-7.5 (m, 2H), 6.10 (t, J = 6.9 Hz, 1H), 5.95 (bs, 1H), 4.17 (t, J = 6.6 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-185 (A) δ 7.4-7.55 (m, 6H), 6.58 and 6.34 (s, 1H), 6.10 and 5.99 (bs, 1H), 4.49 and 4.30 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.50 and 2.48 (s, 3H). 5-186 (A) δ 7.35-7.55 (m, 6H), 6.03 (bs, 1H), 4.27 (q, J = 2.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H), 2.30 (t, J = 2.4 Hz, 1H). 5-189 (A) δ 7.25-7.55 (m, 11H), 6.0-6.2 (m, 1H), 5.2-5.4 (m, 1H), 4.06 (d, J = 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.41 (s, 3H), 1.60 (d, J = 6.9 Hz, 3H). 5-191 (A) δ 7.2-7.6 (m, 11H), 6.09 (bs, 1H), 5.06 (q, J = 7.5 Hz, 1H), 4.06 (d, J = 17.1 Hz, 1H), 3.68 (d, J = 17.1 Hz, 1H), 2.40 (s, 3H), 1.85-2.0 (m, 2H), 0.97 (t, J = 7.2 Hz, 3H). 5-194 (B) δ 7.3-7.6 (m, 11H), 6.42 (d, J = 9.6 Hz, 1H), 6.26 (d, J = 9.6 Hz, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.85-3.95 (m, 1H), 3.7-3.8 (m, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H). 5-205 (A) δ 7.35-7.55 (m, 7H), 6.25-6.35 (m, 2H), 6.10 (bs, 1H), 4.62 (d, J = 5.4 Hz, 2H), 4.07 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.46 (s, 3H). 5-207 (A) δ 7.3-7.55 (m, 6H), 6.7-6.8 (m, 2H), 6.39 (bs, 1H), 4.64 (d, J = 6.0 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H). 5-208 (A) δ 7.4-7.6 (m, 6H), 6.37 (bs, 1H), 6.04 (s, 1H), 4.66 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H), 2.43 (s, 3H). 5-209 (A) δ 7.35-7.6 (m, 6H), 6.57 (t, J = 6.0 Hz, 1H), 6.31 (s, 1H), 4.70 (d, J = 6.0 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H). 5-212 (A) δ 7.56 (s, 1H), 7.35-7.55 (m, 6H), 5.90 (bs, 1H), 4.46 (d, J = 5.4 Hz, 2H), 4.07 (d, J = 17.1 Hz, 1H), 3.85 (s, 3H), 3.68 (d, J = 17.1 Hz, 1H), 2.47 (s, 3H). 5-213 (A) δ 7.3-7.55 (m, 6H), 6.19 (bs, 1H), 4.43 (d, J = 5.4 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.78 (s, 3H), 3.72 (d, J = 17.1 Hz, 1H), 2.43 (s, 3H). 5-216 (A) δ 7.74 (d, J = 3.3 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (bs, 1H), 7.40 (d, J = 3.3 Hz, 1H), 6.66 (bs, 1H), 4.95 (d, J = 5.4 Hz, 2H), 4.08 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-217 (A) δ 7.75 (d, J = 3.3 Hz, 1H), 7.3-7.6 (m, 13H), 6.59 (d, J = 7.4 Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.69 (d, J = 17.3 Hz, 1H), 2.46 (s, 3H). 5-218 (A) δ 7.76 (s, 1H), 7.4-7.75 (m, 6H), 6.78 (bs, 1H), 4.93 (d, J = 3.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H). 5-220 (A) δ 7.4-7.55 (m, 6H), 7.17 (s, 1H), 6.40 (bs, 1H), 4.64 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H), 2.46 (s, 3H). 5-221 (A) δ 7.4-7.55 (m, 6H), 7.07 (s, 1H), 6.42 (bs, 1H), 4.66 (d, J = 5.4 Hz, 2H), 4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H), 2.70 (s, 3H), 2.47 (s, 3H). 5-222 (A) δ 8.76 (s, 1H), 7.81 (s, 1H), 7.50 (bs, 4H), 7.35-7.45 (m, 2H), 6.36 (bs, 1H), 4.83 (d, J = 6.0 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.46 (s, 3H). 5-223 (A) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 3H), 6.27 (t, J = 6.0 Hz, 1H), 4.71 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-224 (B) δ 7.91 (bs, 1H), 7.4-7.55 (m, 6H), 6.84 (s, 1H), 6.79 (s, 1H), 4.66 (d, J = 4.9 Hz, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.80 (s, 3H), 3.77 (d, J = 17.0 Hz, 1H), 2.45 (s, 3H). 5-225 (B) δ 7.25-7.55 (m, 7H), 6.9-7.0 (m, 1H), 6.84 (s, 1H), 4.57 (d, J = 5.5 Hz, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.63 (s, 3H), 2.42 (s, 3H). 5-226 (B) δ 8.62 (s, 1H), 7.35-7.65 (m, 6H), 6.8-6.9 (m, 1H), 5.07 (d, J = 6.1 Hz, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 2.42 (s, 3H). 5-227 (B) δ 7.45-7.55 (m, 5H), 7.35-7.4 (m, 1H), 6.9-6.95 (m, 1H), 4.80 (d, J = 5.8 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.68 (s, 3H), 2.41 (s, 3H). 5-230 (A) δ 8.43 (s, 1H), 7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.68 (t, J = 5.7 Hz, 1H), 4.90 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.48 (s, 3H). 5-231 (A) δ 7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.78 (t, J = 5.7 Hz, 1H), 4.80 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.54 (s, 3H), 2.47 (s, 3H). 5-232 (A) δ 9.14 (s, 1H), 7.45-7.55 (m, 6H), 6.85 (t, J = 5.7 Hz, 1H), 5.09 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-233 (B) δ 8.42 (s, 1H), 8.05-8.15 (m, 1H), 7.87 (s, 1H), 7.35-7.55 (m, 6H), 5.70 (d, J = 6.4 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.32 (s, 3H). 5-235 (A) δ 8.52 (d, J = 4.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.55 (m, 9H), 5.32 (dq, J = 6.9 Hz, 1H), 4.09 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.59 (d, J = 6.9 Hz, 3H). 5-238 (B) δ 7.66 (t, J = 7.7 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.25-7.35 (m, 2H), 7.02 (t, J = 5.3 Hz, 1H), 4.69 (d, J = 5.3 Hz, 2H), 4.10 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H). 5-239 (B) δ 8.2-8.3 (m, 1H), 7.55-7.65 (m, 2H), 7.45-7.55 (m, 3H), 7.4-7.5 (m, 3H), 7.25-7.4 (m, 2H), 4.79 (d, J = 6.2 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.41 (s, 3H). 5-240 (A) δ 8.58 (d, J = 1.8 Hz, 1H), 8.53 (dd, J = 4.8, 1.8 Hz, 1H), 7.72 (d, J = 7.8 Hz, 1H), 7.4-7.55 (m, 6H), 7.30 (dd, J = 7.8, 4.8 Hz, 1H), 6.40 (t, J = 6.0 Hz, 1H), 4.63 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-242 (A) δ 8.57 (d, J = 6.0 Hz, 2H), 7.4-7.55 (m, 6H), 7.26 (d, J = 6.0 Hz, 2H), 6.42 (t, J = 6.0 Hz, 1H), 4.64 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-243 (A) δ 8.73 (d, J = 5.4 Hz, 2H), 7.5-7.6 (m, 5H), 7.43 (s, 1H), 7.24 (t, J = 5.4 Hz, 1H), 7.19 (bs, 1H), 4.89 (d, J = 5.2 Hz, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.53 (s, 3H). 5-245 (A) δ 9.18 (bs, 1H), 8.73 (d, J = 5.2 Hz, 1H), 7.56 (s, 3H), 7.52 (bs, 2H), 7.4-7.45 (m, 1H), 7.35-7.4 (m, 1H), 7.04 (bs, 1H), 4.77 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.52 (s, 3H). 5-246 (B) δ 8.69 (s, 1H), 8.53 (s, 2H), 7.5-7.55 (m, 5H), 7.4-7.45 (m, 1H), 6.95-7.0 (m, 1H), 4.81 (d, J = 5.3 Hz, 2H), 4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.49 (s, 3H). 5-247 (B) δ 8.55-8.6 (m, 1H), 8.35-8.4 (m, 1H), 7.4-7.55 (m, 6H), 6.95-7.05 (m, 1H), 4.75-4.8 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.57 (s, 3H), 2.46 (s, 3H). 5-265 (B) δ 7.5-7.55 (m, 5H), 7.4-7.45 (m, 1H), 6.70 (bs, 1H), 4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 2.51 (s, 3H), 1.51 (s, 9H). 5-277 (C) δ 7.45-7.65 (m, 6H), 7.44 (s, 1H), 7.33 (d, J = 7.8 Hz, 1H), 7.21 (t, J = 7.8 Hz, 1H), 7.00 (d, J = 7.8 Hz, 1H), 6.89 (t, J = 7.8 Hz, 1H), 6.69 (s, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.61 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-278 (C) δ 7.45-7.65 (m, 6H), 7.44 (s, 1H), 7.20 (t, J = 8.4 Hz, 1H), 6.85-6.95 (m, 2H), 6.81 (d, J = 8.4 Hz, 1H), 6.33 (s, 1H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H). 5-279 (A) δ 7.95 (s, 1H), 7.35-7.55 (m, 6H), 7.17 (d, J = 8.4 Hz, 2H), 6.79 (d, J = 8.4 Hz, 2H), 6.42 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H). 5-280 (A) δ 7.4-7.65 (m, 10H), 6.98 (d, J = 8.4 Hz, 2H), 4.10 (d, J = 17.3 Hz, 1H), 3.72 (d, J = 17.3 Hz, 1H), 2.52 (s, 3H). 5-296 (A) δ 8.76 (bs, 1H), 8.12 (bs, 1H), 8.02 (d, J = 5.4 Hz, 1H), 7.35-7.5 (m, 6H), 6.26 (d, J = 5.4 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H), 2.43 (s, 3H). 5-299 (C) δ 10.15 (bs, 1H), 9.37 (bs, 1H), 8.40 (s, 1H), 7.5-7.6 (m, 5H), 7.46 (s, 1H), 6.69 (s, 1H), 4.17 (d, J = 17.4 Hz, 1H), 3.86 (d, J = 17.4 Hz, 1H), 2.59 (s, 3H). 5-301 (A) δ 7.4-7.65 (m, 7H), 7.34 (d, J = 9.3 Hz, 1H), 7.01 (d, J = 9.3 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 4.13 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H). 5-303 (B) δ 10.38 (bs, 1H), 7.2-8.65 (m, 11H), 4.05-4.2 (m, 1H), 3.7-3.85 (m, 1H), 2.44 and 2.37 (s, 3H). 5-311 (A) δ 7.3-7.75 (m, 6H), 6.52 (t, J = 6.3 Hz, 1H), 4.05-4.2 (m, 3H), 3.77 (d, J = 17.4 Hz, 1H), 2.60 (s, 3H). 5-312 (A) δ 7.25-7.65 (m, 6H), 6.54 (t, J = 6.3 Hz, 1H), 3.9-4.15 (m, 2H), 4.10 (d, J = 17.7 Hz, 1H), 3.73 (d, J = 17.7 Hz, 1H), 2.74 (q, J = 7.2 Hz, 2H), 1.19 (t, J = 7.2 Hz, 3H). 5-313 (A) δ 8.50 (d, J = 4.8 Hz, 1H), 7.70 (t, J = 4.5 Hz, 1H), 7.5-7.6 (m, 3H), 7.49 (bs, 2H), 7.42 (bs, 1H), 7.15-7.35 (m, 3H), 4.73 (d, J = 4.5 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.84 (q, J = 7.5 Hz, 2H), 1.23 (t, J = 7.5 Hz, 3H). 5-316 (B) δ 7.72 (bs, 3H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H), 7.15-7.25 (m, 1H), 4.71 (d, J = 6.0 Hz, 2H), 4.15-4.2 (m, 3H), 3.73 (d, J = 17.2 Hz, 1H), 3.34 (t, J = 6.0 Hz, 1H). 5-318 (A) δ 8.30 (d, J = 8.4 Hz, 1H), 8.18 (bs, 1H), 7.51 (s, 2H), 7.48 (s, 1H), 7.25-7.45 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 4.68 (d, J = 5.7 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.97 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H). 5-320 (B) δ 8.11 (d, J = 8.0 Hz, 1H), 7.70 (s, 1H), 7.64 (d, J = 8.0 Hz, 1H), 7.51 (s, 2H), 7.45 (s, 1H), 6.86 (t, J = 6.0 Hz, 1H), 4.0-4.25 (m, 3H), 3.71 (d, J = 17.6, 1H). 5-322 (A) δ 8.14 (t, J = 7.8 Hz, 1H), 7.54 (d, J = 7.8 Hz, 1H), 7.50 (d, J = 7.8 Hz, 1H), 7.34 (s, 1H), 7.31 (s, 1H), 7.23 (s, 1H), 7.09 and 7.05 (t, J = 6.3 Hz, 1H), 4.18 (qd, J = 18.5, 6.3 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H). 5-325 (A) δ 8.59 (bs, 1H), 8.32 (s, 1H), 8.11 (bs, 1H), 8.03 (d, J = 8.1 Hz, 1H), 7.85 (d, J = 8.1 Hz, 1H), 7.73 (t, J = 8.1 Hz, 1H), 7.51 (bs, 2H), 7.43 (bs, 1H), 7.2-7.4 (m, 2H), 4.73 (bs, 2H), 4.23 and 4.21 (d, J = 17.4 Hz, 1H), 3.86 and 3.85 (d, J = 17.4 Hz, 1H), 2.96 and 2.93 (s, 3H). 5-328 (A) δ 8.16 (t, J = 8.0 Hz, 1H), 7.6-7.8 (m, 3H), 7.56 (d, J = 8.0 Hz, 1H), 7.52 (d, J = 8.1 Hz, 1H), 7.08 and 7.03 (t, J = 6.5 Hz, 1H), 4.35-4.55 (m, 2H), 4.05-4.25 (m, 2H), 4.14 (d, J = 17.4 Hz, 1H), 3.79 (d, J = 17.4 Hz, 1H). 5-330 (B) δ 8.57 (d, J = 4.8 Hz, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.62 (t, J = 4.6 Hz, 1H), 7.54 (d, J = 8.6 Hz, 1H), 7.50 (d, J = 1.6 Hz, 2H), 7.42 (t, J = 1.8 Hz, 1H), 7.33 (d, J = 7.9 Hz, 1H), 7.24 (dd, J = 7.5, 5.0 Hz, 1H), 6.9-7.0 (m, 2H), 5.73 (bs, 2H), 4.72 (d, J = 4.8 Hz, 2H), 4.04 (d, J = 17.2 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H). 5-332 (A) δ 8.57 (d, J = 4.2 Hz, 1H), 7.65-7.75 (m, 2H), 7.45-7.6 (m, 4H), 7.43 (bs, 1H), 7.33 (d, J = 7.8 Hz, 1H), 7.2-7.3 (m, 1H), 6.93 (bs, 1H), 6.85 (d, J = 7.8 Hz, 1H), 4.71 (d, J = 4.8 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.90 (d, J = 3.6 Hz, 3H). 5-335 (A) δ 10.29 (bs, 1H), 8.56 (d, J = 6.0 Hz, 1H), 8.18 (d, J = 8.1 Hz, 1H), 7.15-7.75 (m, 8H), 4.79 (d, J = 5.4 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.75 (s, 6H). 5-336 (A) δ 8.45-8.6 (m, 1H), 8.23 and 8.29 (s, 1H), 7.15-7.9 (m, 10H), 4.65-4.75 (m, 2H), 4.0-4.2 (m, 1H), 3.6-3.8 (m, 1H), 3.25 and 3.34 (s, 3H). 5-337 (A) δ 8.45-8.6 (m, 1H), 7.15-8.05 (m, 10H), 4.65-4.75 (m, 2H), 4.0-4.2 (m, 1H), 3.65-3.8 (m, 1H), 3.33 and 3.22 (s, 3H), 2.19 and 1.87 (s, 3H). 5-340 (B) δ 7.95-8.0 (m, 1H), 7.89 (dd, J = 8.0, 2.6 Hz, 1H), 7.79 (dd, J = 7.8, 1.6 Hz, 1H), 7.52 (bs, 2H), 7.44 (t, J = 1.8 Hz, 1H), 5.51 (s, 1H), 4.45-4.55 (m, 1H), 4.14 (dd, J = 20.2, 7.6 Hz, 1H), 3.9-4.05 (m, 1H), 3.77 (dd, J = 17.4, 5.2 Hz, 1H). 5-342 (B) δ 7.9-7.95 (bs, 2H), 7.53 (d, J = 1.8 Hz, 1H), 7.44 (dd, J = 8.2, 1.8 Hz, 1H), 7.21 (bs, 2H), 7.14 (t, J = 1.8 Hz, 1H), 3.75-3.9 (m, 3H), 0.30 (s, 9H). 5-343 (B) δ 7.25-7.8 (m, 11H), 5.65 (t, J = 6.0 Hz, 1H), 4.10 (d, J = 17.2 Hz, 1H), 3.7-3.85 (m, 3H). 5-345 (A) δ 8.47 (s, 1H), 8.43 (d, J = 4.8 Hz, 1H), 7.95 (s, 1H), 7.6-7.85 (m, 5H), 7.50 (bs, 2H), 7.43 (bs, 1H), 7.15-7.25 (m, 2H), 4.55 (d, J = 5.4 Hz, 2H), 4.13 (d, J = 17.7 Hz, 1H), 3.77 (d, J = 17.7 Hz, 1H). 5-346 (B) δ 7.91 (ddd, J = 8.6, 6.8, 1.8 Hz, 1H), 7.78 (ddd, J = 8.6, 6.8, 1.8 Hz, 1H), 7.49 (d, J = 1.6 Hz, 2H), 7.45 (t, J = 2.0 Hz, 1H), 6.84 (bs, 1H), 4.15-4.25 (m, 3H), 3.80 (bs, 1H). 5-347 (B) δ 7.85-7.95 (m, 1H), 7.7-7.8 (m, 1H), 7.25-7.5 (m, 8H), 6.90 (bs, 1H), 4.68 (d, J = 5.4 Hz, 2H), 4.16 (bs, 1H), 3.78 (bs, 1H). 5-348 (B) δ 8.59 (bs, 1H), 8.11 (bs, 1H), 7.89 (bs, 1H), 7.71 (bs, 2H), 7.2-7.5 (m, 5H), 4.80 (bs, 2H), 4.18 (d, J = 17.8 Hz, 1H), 3.80 (d, J = 17.8 Hz, 1H). 5-352 (A) δ 8.49 (d, J = 4.5 Hz, 1H), 7.65-7.75 (m, 1H), 7.51 (s, 2H), 7.42 (s, 1H), 7.3-7.4 (m, 3H), 7.22 (dd, J = 7.5, 4.5 Hz, 1H), 7.10 (bs, 1H), 4.76 (d, J = 4.5 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.33 (s, 6H). 5-353 (A) δ 8.77 (d, J = 2.4 Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.70 (s, 1H), 7.60 (d, J = 8.1 Hz, 1H), 7.52 (bs, 2H), 7.43 (bs, 1H), 7.33 (d, J = 2.4 Hz, 1H), 7.10 (t, J = 5.4 Hz, 1H), 4.81 (d, J = 5.4 Hz, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H). 5-354 (A) δ 8.53 (d, J = 4.5 Hz, 1H), 7.55-7.8 (m, 5H), 7.53 (bs, 2H), 7.43 (bs, 1H), 7.2-7.4 (m, 2H), 4.77 (d, J = 4.8 Hz, 2H), 4.13 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 5-356 (A) δ 7.4-7.6 (m, 6H), 6.17 (bs, 1H), 4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H), 3.55-3.7 (m, 4H), 3.53 (q, J = 7.1 Hz, 2H), 2.47 (s, 3H), 1.20 (t, J = 7.1 Hz, 3H). 5-357 (A) δ 7.4-7.6 (m, 6H), 5.97 (t, J = 5.6 Hz, 1H), 4.50 (t, J = 5.6 Hz, 1H), 4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H), 3.60 (t, J = 5.6 Hz, 2H), 3.43 (s, 6H), 2.48 (s, 3H). 5-358 (A) δ 7.4-7.6 (m, 6H), 5.75-6.0 (m, 2H), 5.27 (d, J = 17.1 Hz, 1H), 5.21 (d, J = 10.2 Hz, 1H), 4.0-4.2 (m, 3H), 3.72 (d, J = 17.3 Hz, 1H), 2.48 (s, 3H). 5-359 (A) δ 8.79 (d, J = 2.1 Hz, 1H), 7.3-7.6 (m, 7H), 6.54 (t, J = 5.4 Hz, 1H), 4.77 (d, J = 5.4 Hz, 2H), 4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H), 2.47 (s, 3H). 5-360 (A) δ 8.54 (d, J = 5.0 Hz, 1H), 7.65-7.8 (m, 1H), 7.15-7.6 (m, 9H), 4.74 (d, J = 5.0 Hz, 2H), 4.08 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H), 2.50 (s, 3H). 5-361 (B) δ 7.5-7.55 (m, 4H), 7.43 (d, J = 5.0 Hz, 1H), 7.42 (d, J = 1.8 Hz, 1H), 6.07 (t, J = 6.4 Hz, 1H), 4.27 (d, J = 17.4 Hz, 1H), 4.05-4.15 (m, 2H), 3.68 (dd, J = 17.4, 1.8 Hz, 1H), 2.46 (s, 3H). 5-362 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.6, 1.6 Hz, 1H), 7.5-7.55 (m, 4H), 7.42 (t, J = 1.6 Hz, 1H), 7.34 (d, J = 7.8 Hz, 1H), 7.2-7.3 (m, 3H), 4.75 (d, J = 4.8 Hz, 2H), 4.27 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H). 5-364 (A) δ 7.3-7.6 (m, 6H), 6.07 (t, J = 6.3 Hz, 1H), 3.8-4.25 (m, 7H), 3.41 (d, J = 16.8 Hz, 1H), 2.46 (s, 3H). 5-365 (A) δ 8.52 (d, J = 3.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.6 (m, 9H), 4.75 (d, J = 4.6 Hz, 2H), 3.8-4.2 (m, 5H), 3.41 (d, J = 16.8 Hz, 1H), 2.50 (s, 3H). 5-366 (A) δ 7.3-7.55 (m, 6H), 6.83 (t, J = 6.5 Hz, 1H), 4.20 (d, J = 17.4 Hz, 1H), 4.0-4.15 (m, 2H), 3.62 (d, J = 17.4 Hz, 1H), 2.40 (s, 3H), 2.30 (s, 3H). 5-368 (B) δ 7.5-7.6 (m, 2H), 7.4-7.5 (m, 4H), 6.0-6.5 (m, 1H), 4.1-4.2 (m, 2H), 3.53 (d, J = 3.2 Hz, 2H), 2.50 (s, 3H), 1.64 (d, J = 3.2 Hz, 2H), 0.04 (s, 9H). 5-369 (B) δ 8.55-8.6 (m, 1H), 7.7-7.8 (m, 1H), 7.5-7.55 (m, 3H), 7.35-7.45 (m, 3H), 7.2-7.3 (m, 3H), 4.79 (d, J = 4.8 Hz, 2H), 3.53 (d, J = 3.2 Hz, 2H), 2.55 (s, 3H), 1.64 (d, J = 5.8 Hz, 2H), 0.04 (s, 9H). 5-370 (A) δ 7.47 (s, 1H), 7.45 (d, J = 7.8 Hz, 1H), 7.34 (d, J = 7.8 Hz, 1H), 7.15-7.3 (m, 3H), 6.28 (t, J = 6.5 Hz, 1H), 4.07 (qd, J = 18.5, 6.5 Hz, 2H), 3.61 (d, J = 16.2 Hz, 1H), 3.53 (d, J = 16.2 Hz, 1H), 2.40 (s, 3H), 0.11 (s, 9H). 5-371 (A) δ 8.50 (d, J = 5.1 Hz, 1H), 7.45-7.75 (m, 4H), 7.15-7.35 (m, 6H), 4.72 (d, J = 5.1 Hz, 2H), 3.63 (d, J = 16.2 Hz, 1H), 3.54 (d, J = 16.2 Hz, 1H), 2.48 (s, 3H), 0.11 (s, 9H). 5-372 (A) δ 8.60 (d, J = 4.7 Hz, 1H), 7.15-7.75 (m, 9H), 6.05 (t, J = 6.0 Hz, 1H), 4.77 (d, J = 16.8 Hz, 1H), 4.0-4.2 (m, 2H), 3.69 (d, J = 16.8 Hz, 1H), 2.45 (s, 3H). 5-373 (A) δ 8.60 (d, J = 4.9 Hz, 1H), 8.53 (d, J = 5.1 Hz, 1H), 7.15-7.8 (m, 13H), 4.7-4.85 (m, 3H), 3.69 (d, J = 16.7 Hz, 1H), 2.48 (s, 3H). 5-374 (A) δ 7.3-7.75 (m, 6H), 6.0-6.5 (br, 1H), 3.95-4.25 (m, 3H), 3.70 (d, J = 17.1 Hz, 1H), 2.42 (s, 3H). 5-375 (A) δ 8.55 (d, J = 4.8 Hz, 1H), 7.45-7.75 (m, 7H), 7.3-7.45 (m, 2H), 7.15-7.3 (m, 1H), 4.74 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-377 (A) δ 8.53 (d, J = 4.5 Hz, 1H), 7.55-7.8 (m, 8H), 7.15-7.4 (m, 2H), 4.77 (d, J = 4.5 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H). 5-378 (A) δ 7.65-7.8 (m, 3H), 7.4-7.6 (m, 3H), 6.04 (t, J = 6.3 Hz, 1H), 4.0-4.2 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 2.47 (s, 3H). 5-379 (A) δ 7.73 (bs, 1H), 7.71 (bs, 2H), 7.51 (s, 1H), 7.49 (d, J = 8.7 Hz, 1H), 7.42 (d, J = 8.7 Hz, 1H), 6.2-6.3 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.5-3.65 (m, 4H), 3.38 (s, 3H), 2.45 (s, 3H). 5-380 (A) δ 7.74 (bs, 1H), 7.71 (bs, 2H), 7.51 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.42 (d, J = 8.4 Hz, 1H), 6.2-6.3 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.55-3.65 (m, 4H), 3.53 (q, J = 7.2 Hz, 2H), 2.46 (s, 3H), 1.20 (t, J = 7.2 Hz, 3H). 5-381 (A) δ 7.73 (bs, 1H), 7.70 (bs, 2H), 7.51 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.41 (d, J = 8.4 Hz, 1H), 6.06 (t, J = 5.4 Hz, 1H), 4.50 (t, J = 5.4 Hz, 1H), 4.08 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 16.8 Hz, 1H), 3.59 (t, J = 5.4 Hz, 2H), 3.43 (s, 6H), 2.46 (s, 3H). 5-382 (A) δ 7.73 (bs, 1H), 7.71 (bs, 2H), 7.50 (s, 1H), 7.49 (d, J = 8.7 Hz, 1H), 7.45 (d, J = 8.7 Hz, 1H), 6.47 (t, J = 5.4 Hz, 1H), 4.20 (d, J = 5.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.80 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-385 (A) δ 7.74 (bs, 1H), 7.70 (bs, 2H), 7.49 (s, 1H), 7.48 (d, J = 8.7 Hz, 1H), 7.39 (d, J = 8.7 Hz, 1H), 6.06 (t, J = 5.4 Hz, 1H), 5.92 (ddd, J = 15.9, 10.2, 5.4 Hz, 1H), 5.26 (d, J = 15.9 Hz, 1H), 5.19 (d, J = 10.2 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H), 4.05 (t, J = 5.4 Hz, 2H), 3.71 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H). 5-386 (A) δ 8.76 (d, J = 2.1 Hz, 1H), 7.73 (bs, 1H), 7.70 (bs, 2H), 7.49 (s, 1H), 7.48 (d, J = 8.1 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.29 (d, J = 2.1 Hz, 1H), 6.75 (t, J = 5.4 Hz, 1H), 4.76 (d, J = 5.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H). 5-387 (A) δ 8.53 (d, J = 5.1 Hz, 1H), 7.65-7.8 (m, 4H), 7.53 (s, 3H), 7.33 (d, J = 8.1 Hz, 1H), 7.15-7.3 (m, 2H), 4.75 (d, J = 4.8 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.51 (s, 3H). 5-388 (A) δ 8.5-8.55 (m, 1H), 7.65-7.75 (m, 1H), 7.5-7.6 (m, 3H), 7.2-7.45 (m, 6H), 4.75 (d, J = 4.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.51 (s, 3H), 2.39 (s, 3H). 5-389 (A) δ 8.09 (s, 2H), 7.98 (s, 1H), 7.45-7.55 (m, 2H), 7.38 (d, J = 8.4 Hz, 1H), 6.35 (bs, 1H), 4.21 (d, J = 17.4 Hz, 1H), 4.0-4.15 (m, 2H), 3.77 (d, J = 17.4 Hz, 1H), 2.42 (s, 3H). 5-390 (A) δ 8.53 (d, J = 4.2 Hz, 1H), 8.10 (s, 2H), 7.97 (s, 1H), 7.65-7.8 (m, 1H) 7.54 (bs, 3H), 7.2-7.35 (m, 3H), 4.75 (d, J = 4.5 Hz, 2H), 4.22 (d, J = 17.1 Hz, 1H), 3.77 (d, J = 17.1 Hz, 1H), 2.50 (s, 3H). 5-391 (A) δ 8.52 (d, J = 5.1 Hz, 1H), 7.72 (t, J = 4.8 Hz, 1H), 7.52 (bs, 3H), 7.15-7.35 (m, 4H), 7.07 (d, J = 9.3 Hz, 1H), 6.96 (d, J = 9.3 Hz, 1H), 4.73 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H), 2.50 (s, 3H). 5-392 (A) δ 8.53 (d, J = 4.8 Hz, 1H), 7.6-7.75 (m, 4H), 7.3-7.4 (m, 4H), 7.15-7.35 (m, 2H), 4.77 (d, J = 5.1 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H), 2.50 (s, 3H). 5-393 (A) δ 8.52 (d, J = 4.5 Hz, 1H), 7.70 (t, J = 4.8 Hz, 1H), 7.53 (bs, 1H), 7.52 (bs, 2H), 7.15-7.45 (m, 6H), 4.74 (d, J = 4.8 Hz, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.89 (s, 3H), 3.75 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-394 (A) δ 8.52 (d, J = 5.1 Hz, 1H), 7.70 (t, J = 4.8 Hz, 1H), 7.52 (bs, 3H), 7.15-7.35 (m, 5H), 7.13 (bs, 1H), 4.74 (d, J = 4.8 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.51 (s, 6H), 2.50 (s, 3H). 5-398 (A) δ 8.56 (d, J = 4.5 Hz, 1H), 7.72 (td, J = 7.5, 1.5 Hz, 1H), 7.65 (s, 2H), 7.45-7.6 (m, 4H), 7.39 (d, J = 7.8 Hz, 1H), 7.15-7.3 (m, 1H), 4.72 (d, J = 5.1 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-399 (B) δ 7.35-7.55 (m, 6H), 6.12 (bs, 1H), 4.18 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 3H), 2.4-2.55 (m, 5H). 5-400 (B) δ 7.4-7.6 (m, 6H), 6.87 (d, J = 9.2 Hz, 1H), 5.9-6.0 (m, 1H), 4.08 (dd, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-401 (B) δ 7.4-7.6 (m, 6H), 6.27 (d, J = 10.4 Hz, 1H), 5.6-5.8 (m, 1H), 4.08 (d, J = 17.6 Hz, 1H), 3.71 (d, J = 17.6 Hz, 1H), 3.61 (s, 3H), 2.50 (s, 3H). 5-403 (A) δ 7.35-7.7 (m, 6H), 6.8 (s, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 3.55 (q, J = 5.4 Hz, 2H), 2.74 (t, J = 5.7 Hz, 2H), 2.60 (bs, 4H), 2.45 (s, 3H), 1.79 (bs, 4H). 5-404 (A) δ 7.35-7.6 (m, 6H), 6.77 (s, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 3.53 (q, J = 5.7 Hz, 2H), 2.57 (t, J = 6.0 Hz, 2H), 2.47 (bs, 7H), 1.55-1.65 (m, 4H), 1.35-1.5 (m, 2H). 5-405 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.56 (d, J = 5.7 Hz, 1H), 4.58 (ddd, J = 10.6, 8.4, 5.7 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95-4.05 (m, 1H), 3.8-3.9 (m, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.5-3.65 (m, 2H), 2.85-2.9 (m, 1H), 2.48 (s, 3H), 2.0-2.15 (m, 1H). 5-406 (B) δ 7.4-7.55 (m, 6H), 6.52 (t, J = 6.0 Hz, 1H), 5.35 (bs, 1H), 4.8-4.95 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.6-3.95 (m, 3H), 3.75 (d, J = 17.4 Hz, 1H), 3.4-3.5 (m, 1H), 2.45 (s, 3H). 5-407 (B) δ 7.5-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.84 (d, J = 7.0 Hz, 1H), 5.37 (d, J = 7.1 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.87 (s, 6H), 3.72 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H). 5-409 (A) δ 9.80 and 8.65 (bs, 1H), 7.4-7.6 (m, 6H), 7.1 and 6.64 (bs, 1H), 5.94 (bs, 1H), 5.2-5.5 (m, 2H), 3.95-4.45 (m, 5H), 3.73 (d, J = 17.0 Hz, 1H), 2.42 (s, 3H). 5-410 (B) δ 7.4-7.55 (m, 6H), 6.72 (bs, 1H), 6.37 (bs, 1H), 4.65 (q, J = 7.4 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.25-3.35 (m, 2H), 2.45 (s, 3H), 1.47 (d, J = 7.4 Hz, 3H), 1.16 (t, J = 7.4 Hz, 3H). 5-414 (B) δ 8.19 (t, J = 6.0 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.21 (d, J = 7.5 Hz, 1H), 4.93 (ddd, J = 11.9, 7.5, 4.2 Hz, 1H), 4.31 (bs, 1H), 4.09 (d, J = 17.2 Hz, 1H), 4.0-4.1 (m, 1H), 3.65-3.9 (m, 3H), 3.72 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 2.15-2.25 (m, 1H), 1.8-1.9 (m, 1H). 5-415 (B) δ 7.67 (t, J = 6.6 Hz, 1H), 7.3-7.55 (m, 6H), 7.11 (d, J = 8.1 Hz, 1H), 4.9-5.0 (m, 1H), 4.3-4.45 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.8-3.9 (m, 2H), 3.73 (d, J = 17.2 Hz, 1H), 3.03 (s, 3H), 2.33 (s, 3H), 2.2-2.4 (m, 2H). 5-417 (B) δ 7.3-7.6 (m, 11H), 6.32 (d, J = 9.6 Hz, 1H), 6.24 (d, J = 9.6 Hz, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.59 (s, 3H), 2.51 (s, 3H). 5-420 (A) δ 8.77 (bs, 1H), 7.35-7.55 (m, 6H), 6.81 (s, 1H), 6.37 (d, J = 9.3 Hz, 1H), 6.31 (s, 1H), 6.15-6.25 (m, 1H), 5.9-6.05 (m, 1H), 4.07 (d, J = 17.3 Hz, 1H), 3.69 (d, J = 17.3 Hz, 1H), 2.43 (s, 3H). 5-421 (A) δ 8.69 (d, J = 4.8 Hz, 1H), 7.51 (s, 5H), 7.43 (s, 1H), 7.25 (d, J = 4.8 Hz, 1H), 6.86 (t, J = 5.7 Hz, 1H), 4.82 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.50 (s, 3H). 5-423 (B) δ 7.72 (d, J = 3.3 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.31 (d, J = 3.3 Hz, 1H), 6.78 (d, J = 7.7 Hz, 1H), 5.55-5.65 (m, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 1.72 (d, J = 6.8 Hz, 3H). 5-424 (A) δ 8.29 (d, J = 9.6 Hz, 1H), 7.4-7.6 (m, 7H), 7.12 (s, 1H), 7.01 (s, 1H), 6.7-6.85 (m, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.38 (s, 3H). 5-425 (B) δ 7.45-7.55 (m, 6H), 7.34 (bs, 1H), 6.89 (bs, 1H), 6.58 (t, J = 4.8 Hz, 1H), 4.52 (d, J = 15.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.67 (s, 3H), 2.46 (s, 3H). 5-426 (B) δ 8.33 (s, 1H), 7.92 (s, 1H), 7.45-7.55 (m, 4H), 7.42 (t, J = 1.8 Hz, 1H), 7.25-7.35 (m, 2H), 6.45-6.55 (m, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.29 (s, 3H), 1.87 (d, J = 6.6 Hz, 3H). 5-427 (A) δ 8.40 (s, 1H), 8.07 (s, 1H), 7.2-7.6 (m, 7H), 6.9-7.1 (m, 1H), 4.08 (d, J = 16.5 Hz, 1H), 3.70 (d, J = 16.5 Hz, 1H), 2.44 (s, 3H). 5-428 (A) δ 7.97 (s, 1H), 7.4-7.65 (m, 6H), 4.54 (q, J = 8.3 Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.49 (s, 3H). 5-434 (A) δ 7.4-7.85 (m, 11H), 4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.53 (s, 3H). 5-450 (A) δ 8.52 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 7.8 Hz, 1H), 7.4-7.6 (m, 5H), 7.15-7.35 (m, 4H), 4.73 (d, J = 4.8 Hz, 2H), 4.49 (s, 1H), 3.99 (d, J = 16.8 Hz, 1H), 3.65-3.85 (m, 3H), 3.3-3.65 (m, 1H), 3.33 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H), 1.16 (t, J = 6.9 Hz, 3H). 5-452 (A) δ 8.68 (s, 1H), 8.59 (s, 1H), 8.25 (s, 1H), 7.4-7.6 (m, 3H), 6.06 (t, J = 6.2 Hz, 1H), 4.24 (d, J = 17.1 Hz, 1H), 4.0-4.2 (m, 2H), 3.79 (d, J = 17.1 Hz, 1H), 2.47 (s, 3H). 5-453 (A) δ 8.69 (s, 1H), 8.58 (s, 1H), 8.55 (d, J = 4.9 Hz, 1H), 8.26 (s, 1H), 7.71 (td, J = 7.5, 1.5 Hz, 1H), 7.2-7.55 (m, 6H), 4.74 (d, J = 4.9 Hz, 2H), 4.25 (d, J = 17.3 Hz, 1H), 3.79 (d, J = 17.3 Hz, 1H), 2.50 (s, 3H). 5-455 (B) δ 8.54 (ddd, J = 4.9, 1.6, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H), 7.5-7.55 (m, 3H), 7.43 (s, 2H), 7.33 (d, J = 7.7 Hz, 1H), 7.2-7.3 (m, 2H), 4.74 (d, J = 4.9 Hz, 2H), 4.63 (bs, 2H), 4.02 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H). 5-456 (B) δ 7.61 (s, 2H), 7.45-7.55 (m, 2H), 7.39 (d, J = 7.9 Hz, 1H), 6.28 (t, J = 6.6 Hz, 1H), 6.24 (bs, 1H), 4.0-4.15 (m, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H), 1.50 (s, 9H). 5-457 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.7, 1.7 Hz, 1H), 7.62 (s, 2H), 7.45-7.55 (m, 3H), 7.34 (d, J = 7.9 Hz, 1H), 7.29 (t, J = 4.8 Hz, 1H), 7.2-7.25 (m, 1H), 6.37 (bs, 1H), 4.75 (d, J = 5.0 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H), 1.50 (s, 9H). 5-460 (B) δ 8.77 (d, J = 2.0 Hz, 1H), 7.71 (d, J = 2.2 Hz, 1H), 7.3-7.55 (m, 6H), 6.67 (t, J = 5.5 Hz, 1H), 4.76 (d, J = 5.7 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.44 (s, 3H). 5-461 (B) δ 8.5-8.55 (m, 1H), 7.5-7.75 (m, 6H), 7.45 (dd, J = 8.6, 2.0 Hz, 1H), 7.35 (d, J = 7.9 Hz, 1H), 7.29 (t, J = 4.8 Hz, 1H), 7.15-7.3 (m, 1H), 4.75 (d, J = 4.8 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.72 (s, 3H). 5-462 (B) δ 7.83 (d, J = 8.1 Hz, 1H), 7.74 (d, J = 1.7 Hz, 1H), 7.62 (dd, J = 8.1, 1.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.44 (t, J = 1.8 Hz, 1H), 6.48 (bs, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H). 5-463 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.27 (t, J = 5.1 Hz, 1H), 7.21 (bs, 1H), 4.27 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.9-4.0 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H). 5-468 (B) δ 8.16 (d, J = 1.7 Hz, 1H), 7.69 (dd, J = 8.1, 1.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.43 (t, J = 1.8 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.21 (t, J = 5.3 Hz, 1H), 7.03 (bs, 1H), 4.24 (d, J = 5.3 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.9-4.0 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H). 5-470 (B) δ 9.22 (bs, 1H), 8.40 (s, 2H), 8.11 (d, J = 1.6 Hz, 1H), 7.74 (dd, J = 8.1, 1.6 Hz, 1H), 7.45-7.55 (m, 3H), 7.44 (t, J = 1.8 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H). 5-471 (A) δ 7.35-7.6 (m, 6H), 5.87 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 3.01 (d, J = 4.8 Hz, 3H), 2.47 (s, 3H). 5-472 (B) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 5.8-6.15 (m, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.84 (tdd, J = 15.0, 6.0, 4.2 Hz, 2H), 3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-473 (B) δ 7.4-7.55 (m, 6H), 6.42 (bs, 1H), 4.87 (d, J = 6.8 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.45 (s, 3H), 2.50 (s, 3H). 5-474 (B) δ 7.4-7.55 (m, 6H), 6.46 (bs, 1H), 4.92 (d, J = 6.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.6-3.75 (m, 3H), 2.49 (s, 3H), 1.25 (t, J = 6.8 Hz, 3H). 5-475 (B) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 6.40 (bs, 1H), 4.92 (d, J = 6.8 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.57 (t, J = 6.6 Hz, 2H), 2.50 (s, 3H), 1.55-1.7 (m, 2H), 0.95 (t, J = 7.4 Hz, 3H). 5-476 (B) δ 7.4-7.55 (m, 6H), 6.51 (bs, 1H), 4.92 (d, J = 6.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.90 (sep, J = 6.0 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H), 1.22 (d, J = 6.0 Hz, 6H). 5-477 (B) δ 7.4-7.55 (m, 6H), 6.50 (t, J = 7.2 Hz, 1H), 4.98 (d, J = 6.8 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H), 1.95-2.05 (m, 2H). 5-478 (B) δ 7.4-7.6 (m, 6H), 6.35-6.55 (m, 1H), 5.75-6.05 (m, 1H), 4.96 (dd, J = 28.0, 7.2 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.65-4.2 (m, 3H), 2.50 (s, 3H). 5-479 (B) δ 7.45-7.55 (m, 6H), 6.56 (t, J = 7.2 Hz, 1H), 5.82 (t, J = 5.6 Hz, 1H), 5.34 (t, J = 5.6 Hz, 1H), 5.03 (d, J = 5.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H), 2.30 (t, J = 7.4 Hz, 1H). 5-481 (B) δ 7.4-7.6 (m, 6H), 6.65 (t, J = 7.2 Hz, 1H), 5.17 (d, J = 5.6 Hz, 2H), 4.37 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H). 5-482 (B) δ 7.4-7.6 (m, 6H), 6.63 (bs, 1H), 4.97 (d, J = 6.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.25-3.8 (m, 8H), 2.50 (s, 3H). 5-483 (B) δ 7.4-7.6 (m, 6H), 6.41 (t, J = 7.2 Hz, 1H), 5.85-6.0 (m, 2H), 5.2-5.5 (m, 3H), 4.95 (d, J = 7.2 Hz, 1H), 4.05-4.2 (m, 2H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-484 (B) δ 7.4-7.55 (m, 6H), 6.51 (t, J = 7.2 Hz, 1H), 5.01 (d, J = 7.2 Hz, 2H), 4.32 (d, J = 2.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (t, J = 17.4 Hz, 1H), 2.51 (s, 3H), 2.47 (t, J = 2.4 Hz, 1H). 5-485 (B) δ 7.25-7.55 (m, 11H), 6.43 (bs, 1H), 5.01 (d, J = 6.8 Hz, 2H), 4.65-4.75 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-486 (B) δ 7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.95 (t, J = 7.2 Hz, 1H), 5.41 (d, J = 7.2 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H), 2.12 (s, 3H). 5-487 (A) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.44 (bs, 1H), 5.6-5.7 (m, 1H), 4.0-4.15 (m, 2H), 3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H), 1.45 (d, J = 6.0 Hz, 3H). 5-488 (A) δ 7.4-7.6 (m, 6H), 6.18 (d, J = 9.4 Hz, 1H), 5.6-5.7 (m, 1H), 4.0-4.2 (m, 3H), 3.71 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H), 1.51 (d, J = 6.0 Hz, 3H). 5-490 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.57 (t, J = 4.8 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.55-3.7 (m, 10H), 3.45-3.5 (m, 2H), 3.25 (s, 3H), 2.47 (s, 3H). 5-492 (A) δ 7.45-7.65 (m, 6H), 5.87 (d, J = 8.4 Hz, 1H), 4.4-4.55 (m, 1H), 4.18 (d, J = 6.9 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H), 2.10 (s, 3H), 1.29 (d, J = 6.9 Hz, 3H). 5-493 (B) δ 7.35-7.55 (m, 6H), 6.21 (d, J = 5.8 Hz, 1H), 5.27 (bs, 1H), 5.10 (bs, 1H), 4.44 (bs, 1H), 4.0-4.25 (m, 3H), 3.5-3.75 (m, 4H), 2.46 (s, 3H), 1.25-1.3 (m, 3H). 5-495 (A) δ 7.3-7.55 (m, 6H), 6.4-6.5 (m, 1H), 4.55-4.7 (m, 1H), 3.65-4.15 (m, 6H), 2.39 (s, 3H), 2.2-2.45 (m, 1H), 1.8-2.0 (m, 1H). 5-496 (A) δ 7.4-7.6 (m, 6H), 6.38 (d, J = 9.0 Hz, 1H), 5.2-5.35 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.95-4.15 (m, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.6-3.75 (m, 1H), 2.46 (s, 3H), 1.85-2.0 (m, 2H), 1.4-1.75 (m, 4H). 5-497 (A) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 2H), 6.10 (bs, 1H), 4.55 (d, J = 6.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H), 2.26 (s, 3H). 5-500 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 7.7 Hz, 1H), 6.70 (t, J = 6.8 Hz, 1H), 4.83 (d, J = 6.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H), 2.40 (s, 3H). 5-501 (B) δ 7.5-7.55 (m, 4H), 7.42 (t, J = 1.8 Hz, 1H), 7.41 (d, J = 8.8 Hz, 1H), 7.20 (t, J = 6.8 Hz, 1H), 5.11 (d, J = 6.8 Hz, 2H), 4.67 (q, J = 7.2 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H), 1.44 (t, J = 7.2 Hz, 3H). 5-502 (B) δ 7.4-7.55 (m, 6H), 6.6-6.65 (m, 1H), 4.56 (d, J = 6.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.15 (q, J = 7.2 Hz, 6H), 2.51 (s, 3H), 1.37 (t, J = 7.2 Hz, 9H). 5-504 (B) δ 7.80 (bs, 1H), 7.45-7.55 (m, 3H), 7.43 (t, J = 1.8 Hz, 1H), 7.3-7.4 (m, 4H), 6.95-7.05 (m, 2H), 6.59 (t, J = 5.3 Hz, 1H), 4.05 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 2H), 3.68 (d, J = 17.2 Hz, 1H), 3.22 (t, J = 6.4 Hz, 2H), 2.44 (s, 3H). 5-505 (B) δ 8.47 (d, J = 4.8 Hz, 2H), 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H), 7.00 (t, J = 4.8 Hz, 1H), 6.85 (t, J = 5.3 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.81 (td, J = 6.2, 5.3 Hz, 2H), 3.71 (d, J = 17.2 Hz, 1H), 3.43 (t, J = 6.2 Hz, 2H), 2.44 (s, 3H). 5-506 (B) δ 8.96 (d, J = 5.0 Hz, 2H), 7.61 (t, J = 5.0 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.75 (t, J = 5.7 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.95-4.1 (m, 2H), 3.85-3.95 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-508 (B) δ 7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.24 (bs, 1H), 4.39 (d, J = 6.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.76 (q, J = 7.2 Hz, 2H), 2.49 (s, 3H), 1.15 (t, J = 7.2 Hz, 3H). 5-509 (A) δ 7.5-7.55 (m, 5H), 7.35-7.5 (m, 2H), 6.37 (bs, 1H), 4.44 (t, J = 6.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.2-3.4 (m, 2H), 2.48 (s, 3H). 5-510 (B) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.04 (bs, 1H), 4.92 (d, J = 6.8 Hz, 2H), 4.44 (q, J = 8.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H), 2.18 (s, 3H). 5-511 (B) δ 7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.89 (bs, 1H), 4.91 (d, J = 6.8 Hz, 2H), 4.15-4.3 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.78 (s, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.18 (s, 3H). 5-521 (B) δ 7.4-7.55 (m, 6H), 6.70 (bs, 1H), 5.2-5.3 (m, 1H), 4.03 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 3.5-3.6 (m, 2H), 3.3-3.4 (m, 2H), 3.03 (q, J = 7.4 Hz, 2H), 2.41 (s, 3H), 1.34 (t, J = 7.2 Hz, 3H). 5-522 (B) δ 7.65 (t, J = 4.0 Hz, 1H), 7.4-7.6 (m, 6H), 6.23 (bs, 1H), 4.40 (q, J = 8.4 Hz, 2H), 4.25-4.3 (m, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-523 (A) δ 7.3-7.7 (m, 7H), 6.44 (d, J = 7.5 Hz, 1H), 4.75-4.9 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.84 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H), 1.44 (d, J = 6.9 Hz, 3H). 5-524 (A) δ 7.4-7.65 (m, 7H), 6.79 (d, J = 7.3 Hz, 1H), 4.8-4.9 (m, 1H), 4.05-4.2 (m, 3H), 3.83 (s, 3H), 3.69 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-525 (B) δ 7.35-7.55 (m, 6H), 6.15 (bs, 1H), 4.05-4.2 (m, 3H), 3.70 (d, J = 17.2 Hz, 1H), 3.49 (q, J = 6.4 Hz, 2H), 2.4-2.5 (m, 5H), 1.9-2.0 (m, 2H), 1.2-1.3 (m, 3H). 5-527 (B) δ 7.45-7.6 (m, 5H), 7.4-7.45 (m, 1H), 7.07 (bs, 1H), 4.05-4.3 (m, 3H), 3.74 (d, J = 17.4 Hz, 1H), 3.35 and 3.47 (q, J = 6.8 Hz, 2H), 2.98 and 3.00 (s, 3H), 2.49 (s, 3H), 1.1-1.3 (m, 3H). 5-528 (B) δ 7.4-7.6 (m, 6H), 7.04 (bs, 1H), 4.24 (d, J = 4.0 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 3.44 (q, J = 6.8 Hz, 2H), 3.33 (q, J = 6.8 Hz, 2H), 2.50 (s, 3H), 1.24 (t, J = 6.8 Hz, 3H), 1.18 (t, J = 6.8 Hz, 3H). 5-532 (A) δ 7.4-7.55 (m, 5H), 7.2-7.25 (m, 1H), 6.66 (bs, 1H), 6.16 (bs, 1H), 4.53 (t, J = 5.0 Hz, 1H), 4.1-4.15 (m, 3H), 3.65-3.75 (m, 3H), 3.5-3.6 (m, 2H), 3.46 (t, J = 5.0 Hz, 2H), 2.48 (s, 3H), 1.22 (t, J = 6.8 Hz, 6H). 5-538 (B) δ 7.4-7.55 (m, 6H), 6.63 (d, J = 7.8 Hz, 1H), 6.29 (bs, 1H), 5.62 (bs, 1H), 4.6-4.8 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 5-546 (A) δ 7.35-7.6 (m, 5H), 7.15-7.3 (m, 1H), 6.95-7.1 (m, 1H), 6.6-6.8 (m, 2H), 5.52 (bs, 1H), 4.44 (bs, 1H), 4.05 (d, J = 17.3 Hz, 1H), 3.75 (s, 3H), 3.65 (d, J = 17.3 Hz, 1H), 2.65-3.2 (m, 4H), 2.39 (s, 3H), 1.2-2.2 (m, 4H). 5-548 (A) δ 7.85 (bs, 1H), 7.45-7.55 (m, 6H), 7.03 (t, J = 6.6 Hz, 1H), 6.56 (s, 1H), 5.72 (d, J = 6.6 Hz, 2H), 4.07 (d, J = 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.39 (s, 3H). 5-555 (B) δ 7.4-7.6 (m, 6H), 7.14 (s, 1H), 6.45 (bs, 1H), 4.6-4.7 (m, 2H), 4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 2.67 (s, 3H), 2.45 (s, 3H). 5-556 (B) δ 7.67 (s, 1H), 7.4-7.5 (m, 6H), 6.70 (bs, 1H), 4.75-4.8 (m, 2H), 4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 3.29 (s, 3H), 2.44 (s, 3H). 5-557 (A) δ 7.4-7.6 (m, 7H), 6.51 (t, J = 6.0 Hz, 1H), 4.77 (dd, J = 6.0, 0.6 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.45 (s, 3H). 5-558 (B) δ 8.59 (s, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.81 (t, J = 5.5 Hz, 1H), 4.90 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.45 (s, 3H). 5-559 (B) δ 8.0-8.05 (m, 2H), 7.35-7.6 (m, 9H), 6.29 (d, J = 6.8 Hz, 2H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.38 (s, 3H). 5-560 (A) δ 7.25-7.7 (m, 8H), 6.99 (d, J = 8.6 Hz, 1H), 6.35-6.5 (m, 1H), 6.25 (bs, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.33 (s, 3H), 1.84 (s, 3H). 5-561 (B) δ 8.75 (bs, 1H), 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.36 (d, J = 8.1 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.89 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H). 5-563 (B) δ 7.5-7.6 (m, 5H), 7.44 (t, J = 1.8 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.41 (s, 3H), 2.52 (s, 3H). 5-564 (B) δ 8.74 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 3.04 (s, 6H), 2.51 (s, 3H). 5-565 (A) δ 8.23 (bs, 1H), 7.35-7.65 (m, 11H), 4.10 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-572 (B) δ 8.10 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (d, J = 8.1 Hz, 1H), 5.20 (tqui, J = 20.1, 4.4 Hz, 1H), 4.5-4.75 (m, 4H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-573 (B) δ 8.15 (bs, 1H), 7.45-7.6 (m, 4H), 7.46 (d, J = 8.4 Hz, 1H), 7.43 (t, J = 1.8 Hz, 1H), 5.05-5.25 (m, 1H), 4.55-4.75 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.65-3.8 (m, 3H), 2.47 (s, 3H). 5-575 (B) δ 8.87 (bs, 1H), 7.4-7.55 (m, 6H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.04 (bs, 6H), 2.44 (s, 3H). 5-581 (A) δ 9.27 (t, J = 5.5 Hz, 1H), 8.74 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.4-7.7 (m, 7H), 7.15-7.3 (m, 2H), 4.65 (d, J = 5.5 Hz, 2H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H). 5-583 (B) δ 8.47 (bs, 1H), 7.4-7.55 (m, 6H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.4-3.55 (m, 4H), 2.44 (s, 3H), 1.9-2.05 (m, 4H). 5-585 (A) δ 7.3-7.7 (m, 11H), 7.18 (t, J = 7.2 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H). 5-588 (A) δ 7.5-7.65 (m, 7H), 7.4-7.45 (m, 2H), 7.08 (t, J = 8.4 Hz, 2H), 4.10 (d, J = 17.3 Hz, 1H), 3.72 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H). 5-591 (A) δ 8.20 (bs, 1H), 7.85 (s, 1H), 7.4-7.6 (m, 6H), 6.9-7.25 (m, 4H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.55 (s, 3H). 5-601 (A) δ 8.04 (s, 1H), 7.81 (d, J = 6.9 Hz, 1H), 7.4-7.65 (m, 9H), 4.10 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.54 (s, 3H). 5-603 (A) δ 8.77 (d, J = 7.4 Hz, 1H), 7.4-7.7 (m, 9H), 7.14 (t, J = 7.4 Hz, 1H), 6.05 (d, J = 6.9 Hz, 1H), 4.15-4.3 (m, 1H), 4.10 (d, J = 17.3 Hz, 1H), 3.71 (d, J = 17.3 Hz, 1H), 2.58 (s, 3H), 1.25 (d, J = 6.9 Hz, 6H). 5-604 (A) δ 7.4-7.6 (m, 7H), 6.85-7.0 (m, 2H), 6.65-6.85 (m, 1H), 4.11 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.55 (s, 3H). 5-605 (A) δ 8.25-8.4 (m, 1H), 7.7-7.75 (m, 1H), 7.55-7.6 (m, 3H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 7.05-7.15 (m, 1H), 6.7-6.85 (m, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.55 (s, 3H). 5-609 (A) δ 7.89 (s, 1H), 7.2-7.7 (m, 9H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.53 (s, 3H). 5-610 (A) δ 7.45-7.65 (m, 8H), 7.44 (s, 1H), 7.17 (s, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H). 5-611 (A) δ 8.36 (dd, J = 6.3, 2.7 Hz, 1H), 7.9-8.05 (m, 1H), 7.80 (s, 1H), 7.4-7.6 (m, 6H), 7.32 (t, J = 9.0 Hz, 1H), 4.11 (d, J = 17.3 Hz, 1H), 3.73 (d, J = 17.3 Hz, 1H), 2.52 (s, 3H). 5-612 (A) δ 7.5-7.7 (m, 5H), 7.44 (t, J = 2.0 Hz, 1H), 7.03 (bs, 1H), 6.80 (t, J = 7.2 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H). 5-615 (A) δ 8.41 (bs, 1H), 7.4-7.65 (m, 6H), 6.74 (bs, 2H), 6.23 (bs, 2H), 4.09 (d, J = 17.0 Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H), 2.53 (s, 3H). 5-617 (A) δ 7.4-7.75 (m, 9H), 6.38 (bs, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H). 5-618 (A) δ 9.23 (bs, 1H), 7.4-7.7 (m, 8H), 4.10 (d, J = 17.3 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-619 (B) δ 9.32 (bs, 1H), 7.45-7.7 (m, 7H), 4.11 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.60 (s, 3H). 5-621 (B) δ 7.4-7.55 (m, 6H), 6.80 (bs, 1H), 4.56 (d, J = 6.4 Hz, 2H), 4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 3.16 (q, J = 7.2 Hz, 6H), 2.51 (s, 3H), 1.37 (t, J = 7.2 Hz, 9H). 5-629 (A) δ 8.4-8.6 (m, 3H), 7.95-8.1 (m, 1H), 7.61 (s, 3H), 7.4-7.55 (m, 3H), 4.12 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H), 2.56 (s, 3H). 5-630 (A) δ 8.29 (d, J = 7.8 Hz, 1H), 8.23 (s, 1H), 7.74 (t, J = 7.8 Hz, 1H), 7.5-7.6 (m, 6H), 7.13 (d, J = 7.2 Hz, 1H), 4.11 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H), 2.55 (s, 3H). 5-631 (A) δ 8.32 (d, J = 8.1 Hz, 1H), 8.21 (s, 1H), 7.2-7.7 (m, 8H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.55 (s, 3H). 5-633 (A) δ 8.46 (s, 1H), 8.27 (d, J = 7.1 Hz, 1H), 7.76 (s, 1H), 7.3-7.6 (m, 7H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.52 (s, 3H). 5-634 (A) δ 8.72 (d, J = 2.4 Hz, 1H), 8.52 (dd, J = 8.4, 2.4 Hz, 1H), 7.99 (s, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.4-7.65 (m, 6H), 4.11 (d, J = 17.3 Hz, 1H), 3.73 (d, J = 17.3 Hz, 1H), 2.54 (s, 3H). 5-635 (A) δ 8.31 (d, J = 5.4 Hz, 1H), 7.81 (s, 1H), 7.75-7.8 (m, 1H), 7.4-7.6 (m, 7H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-637 (A) δ 8.82 (s, 1H), 8.41 (d, J = 4.8 Hz, 1H), 7.4-7.6 (m, 6H), 6.90 (d, J = 4.8 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H), 2.45 (s, 3H). 5-647 (B) δ 7.4-7.55 (m, 4H), 7.37 (d, J = 7.9 Hz, 1H), 6.37 (t, J = 6.0 Hz, 1H), 4.0-4.15 (m, 2H), 4.06 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H), 2.41 (s, 3H). 5-648 (B) δ 8.5-8.6 (m, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.6 (m, 6H), 7.38 (d, J = 7.9 Hz, 1H), 7.2-7.3 (m, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.71 (s, 3H), 2.47 (s, 3H). 5-649 (B) δ 8.55-8.65 (m, 1H), 7.84 (td, J = 7.7, 1.7 Hz, 1H), 7.3-7.8 (m, 8H), 4.78 (d, J = 5.1 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.56 (bs, 1H), 2.49 (s, 3H). 5-651 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.8, 1.8 Hz, 1H), 7.5-7.6 (m, 5H), 7.34 (d, J = 7.9 Hz, 1H), 7.2-7.3 (m, 2H), 4.75 (d, J = 4.8 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.92 (s, 3H), 3.71 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H). 5-652 (B) δ 8.5-8.6 (m, 1H), 7.92 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.7 (m, 6H), 7.39 (d, J = 7.7 Hz, 1H), 7.15-7.3 (m, 1H), 4.71 (d, J = 5.3 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H), 1.57 (s, 9H). 5-653 (B) δ 7.4-7.55 (m, 4H), 7.39 (d, J = 7.9 Hz, 1H), 6.37 (t, J = 5.9 Hz, 1H), 4.0-4.15 (m, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.90 (s, 6H), 2.42 (s, 3H). 5-654 (B) δ 8.5-8.6 (m, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.55 (m, 5H), 7.41 (t, J = 4.8 Hz, 1H), 7.36 (d, J = 7.7 Hz, 1H), 7.2-7.3 (m, 1H), 4.73 (d, J = 5.0 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.90 (s, 6H), 2.48 (s, 3H). 5-655 (A) δ 8.12 (s, 1H), 7.7-7.75 (m, 1H), 7.4-7.5 (m, 4H), 6.73 (bs, 1H), 5.03 (d, J = 6.8 Hz, 2H), 4.13 (q, J = 8.4 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H). 5-656 (A) δ 8.09 (bs, 1H), 7.35-7.75 (m, 5H), 6.27 (bs, 1H), 5.8-5.9 (m, 1H), 3.8-4.2 (m, 3H), 3.69 (d, J = 17.4 Hz, 1H), 2.2-2.35 (m, 1H), 1.9-2.1 (m, 3H). 5-657 (B) δ 8.37 (d, J = 1.7 Hz, 1H), 7.83 (dd, J = 8.1, 1.8 Hz, 1H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 7.35 (bs, 1H), 6.99 (bs, 1H), 4.23 (d, J = 17.8 Hz, 1H), 4.22 (d, J = 5.1 Hz, 2H), 3.9-4.05 (m, 2H), 3.84 (d, J = 17.8 Hz, 1H). 5-658 (A) δ 7.4-7.6 (m, 6H), 5.9-6.0 (m, 2H), 4.9-5.0 (m, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 3.53 (s, 3H), 2.33 (s, 3H), 2.1-2.45 (m, 3H), 1.95-2.05 (m, 1H), 1.6-1.8 (m, 2H). 5-662 (A) δ 8.41 (s, 1H), 7.4-7.55 (m, 6H), 5.67 (t, J = 6.3 Hz, 1H), 4.12 (d, J = 17.4 Hz, 1H), 3.7-3.9 (m, 2H), 3.72 (d, J = 17.4 Hz, 1H), 3.19 (s, 3H), 2.47 (s, 3H). 5-667 (A) δ 8.78 (bs, 1H), 7.75 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (t, J = 1.5 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H). 5-668 (A) δ 8.38 (dd, J = 4.8, 1.5 Hz, 1H), 8.04 (s, 1H), 7.77 (dd, J = 7.8, 1.5 Hz, 1H), 7.65-7.65 (m, 5H), 7.57 (t, J = 1.8 Hz, 1H), 7.12 (dd, J = 7.8, 4.8 Hz, 1H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.58 (s, 3H). 5-669 (A) δ 7.88 (d, J = 8.0 Hz, 1H), 7.74 (s, 1H), 7.64 (d, J = 8.0 Hz, 1H), 7.52 (d, J = 1.5 Hz, 2H), 7.44 (t, J = 1.5 Hz, 1H), 6.38 (bs, 1H), 6.02 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H). 5-670 (A) δ 7.66 (bs, 1H), 7.5-7.6 (m, 5H), 5.74 (bs, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-672 (A) δ 8.09 (s, 2H), 7.97 (s, 1H), 7.5-7.6 (m, 3H), 5.79 (bs, 2H), 4.21 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-677 (A) δ 7.4-7.6 (m, 6H), 5.70 (bs, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.88 (q, J = 7.8 Hz, 2H), 1.26 (t, J = 7.8 Hz, 3H). 5-679 (A) δ 7.35-8.25 (m, 6H), 6.97 (bs, 1H), 6.70 (t, J = 72.3 Hz, 1H), 6.27 (bs, 1H), 4.10 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H). 5-680 (A) δ 7.45-8.0 (m, 6H), 6.80 (bs, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.20 (d, J = 17.4 Hz, 1H). 5-682 (A) δ 11.3 (s, 1H), 7.4-8.85 (m, 8H), 4.15 (d, J = 17.4 Hz, 1H), 3.75 (d, J = 17.4 Hz, 1H), 2.05 (s, 3H). 5-684 (A) δ 7.81 (s, 1H), 7.75 (s, 1H), 7.69 (s, 1H), 7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H), 6.06 (t, J = 6.6 Hz, 1H), 4.05-4.2 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-685 (A) δ 6.58 (d, J = 6.3 Hz, 2H), 7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H), 6.05 (t, J = 6.6 Hz, 1H), 4.05-4.2 (m, 3H), 3.68 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H). 5-686 (A) δ 7.90 (dd, J = 6.3, 2.1 Hz, 1H), 7.75 (d, J = 5.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H), 6.06 (t, J = 6.6 Hz, 1H), 4.05-4.2 (m, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H). 6-001 (A) δ 7.4-7.55 (m, 6H), 6.06 (bs, 1H), 5.39 (d, J = 28.6 Hz, 2H), 4.24 (d, J = 6.0 Hz, 2H), 4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.3 Hz, 1H), 2.49 (s, 3H). 6-003 (A) δ 7.45-7.55 (m, 4H), 7.43 (s, 1H), 7.23 (d, J = 7.8 Hz, 1H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 3.43 (bs, 2H), 3.10 (bs, 2H), 2.32 (s, 3H), 1.26 (t, J = 6.9 Hz, 3H), 1.03 (t, J = 6.9 Hz, 3H). 6-005 (B) δ 7.98 (m, 1H), 7.2-7.6 (m, 6H), 4.09 (d, J = 17.0 Hz, 1H), 3.18 (bs, 1H), 3.71 (d, J = 17.0 Hz, 1H), 3.40 (bs, 1H), 2.43 and 2.33 (s, 3H), 2.12 and 1.66 (s, 3H), 1.23 and 1.08 (bs, 3H). 6-006 (B) δ 7.2-7.6 (m, 6H), 4.05-4.15 (m, 1H), 3.75-3.9 and 3.35-3.5 (m, 2H), 3.7 and 3.8 (m, 1H), 2.41 and 2.38 (s, 3H), 2.23 and 1.80 (s, 3H), 2.00 and 1.77 (s, 3H), 1.25-1.3 and 1.05-1.1 (m, 3H). 6-007 (B) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.2-7.25 (m, 1H), 3.2-4.7 (m, 4H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.35 and 2.33 (s, 3H), 1.65-1.8 and 1.5-1.6 (m, 2H), 1.4-1.5 and 1.1-1.25 (m, 2H), 1.0-1.05 and 0.75-0.85 (m, 3H). 6-008 (B) δ 7.6-7.65 (m, 2H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 7.3-7.35 (m, 1H), 4.65 (bs, 2H), 4.19 (bs, 2H), 4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.37 (s, 3H). 6-010 (B) δ 7.5-7.55 (m, 4H), 7.3-7.5 (m, 7H), 4.85 (bs, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 3.35 (bs, 3H), 2.27 (s, 3H). 6-011 (B) δ 7.4-7.55 (m, 5H), 7.25-7.4 (m, 6H), 4.90 (bs, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H), 1.88 (bs, 3H). 6-012 (B) δ 7.4-7.55 (m, 5H), 7.25-7.4 (m, 6H), 4.43 (bs, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.78 (bs, 3H), 3.68 (d, J = 17.0 Hz, 1H), 2.38 (s, 3H). 6-013 (B) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.3-7.4 (m, 4H), 7.15-7.25 (m, 2H), 4.93 (bs, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 3.05 (bs, 3H), 2.28 (s, 3H). 6-015 (A) δ 8.82 (s, 1H), 7.35-7.6 (m, 6H), 7.08 (s, 1H), 4.75-5.2 (m, 2H), 4.56 (bs, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.79 (d, J = 17.4 Hz, 1H), 2.36 and 2.29 (s, 3H). 6-016 (A) δ 8.80 and 8.77 (d, J = 7.8 Hz, 1H), 7.45-7.55 (m, 4H), 7.3-7.45 (m, 3H), 4.85-5.2 (m, 1H), 4.2-4.7 (m, 2H), 4.07 and 4.08 (d, J = 17.4 Hz, 1H), 3.75-4.0 (m, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.31 and 2.36 (s, 3H), 2.25-2.3 (m, 1H). 6-017 (B) δ 8.72 (s, 1H), 7.5-7.6 (m, 4H), 7.48 (s, 1H), 7.4-7.45 (m, 1H), 7.18 (s, 1H), 5.03 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.35 (s, 3H). 6-018 (A) δ 8.72 (s, 1H), 7.45-7.55 (m, 4H), 7.4-7.45 (m, 1H), 7.31 (d, J = 7.8 Hz, 1H), 7.20 (s, 1H), 5.04 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.75 (q, J = 7.2 Hz, 2H), 2.34 (s, 3H), 1.12 (t, J = 7.2 Hz, 3H). 6-019 (B) δ 8.80 (s, 1H), 7.55-7.6 (m, 4H), 7.42 (s, 1H), 7.25-7.3 (m, 2H), 5.26 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 3.62 (s, 3H), 2.33 (s, 3H). 6-021 (B) δ 8.5-8.6 (m, 1H), 7.65-7.75 (m, 1H), 7.4-7.6 (m, 5H), 7.1-7.35 (m, 3H), 3.0-5.3 (m, 4H), 4.0-4.15 (m, 1H), 3.65-3.8 (m, 1H), 2.37 and 2.34 (s, 3H), 1.25-1.35 and 1.0-1.1 (m, 3H). 6-022 (B) δ 8.55-8.6 (m, 1H), 7.65-7.75 (m, 1H), 7.05-7.55 (m, 8H), 4.3-5.3 (m, 2H), 4.0-4.15 (m, 1H), 2.9-4.1 (m, 2H), 3.65-3.75 (m, 1H), 2.37 and 2.32 (s, 3H), 1.65-1.75 and 1.45-1.55 (m, 2H), 0.95-1.0 and 0.65-0.75 (m, 3H). 6-023 (B) δ 8.55-8.6 and 8.45-8.5 (m, 1H), 7.4-7.7 (m, 7H), 7.25-7.35 (m, 1H), 7.1-7.2 (m, 1H), 4.90 (d, J = 16.0 Hz, 1H), 4.76 (d, J = 16.0 Hz, 1H), 4.0-4.15 (m, 1H), 3.6-3.85 (m, 2H), 2.42 and 2.34 (s, 3H), 1.23 and 1.06 (bs, 6H). 6-024 (B) δ 8.5-8.6 (m, 1H), 7.05-7.7 (m, 9H), 4.83 and 4.39 (s, 2H), 4.0-4.15 (m, 1H), 3.65-3.8 (m, 1H), 2.75-2.85 and 2.65-2.7 (m, 1H), 2.36 and 2.33 (s, 3H), 0.75-0.9 and 0.45-0.6 (m, 4H). 6-025 (B) δ 8.5-8.55 (m, 1H), 7.65-7.7 (m, 1H), 7.15-7.5 (m, 8H), 4.45 and 4.16 (bs, 2H), 4.02 (d, J = 17.0 Hz, 1H), 3.63 (d, J = 17.0 Hz, 1H), 2.38 (s, 3H), 1.54 (s, 9H). 6-026 (B) δ 8.55-8.6 (m, 1H), 7.2-7.75 (m, 8H), 6.92 (d, J = 7.7 Hz, 1H), 3.7-5.25 (br, 4H), 4.1-4.15 (m, 1H), 3.65-3.7 (m, 1H), 2.04 and 2.26 (s, 3H). 6-027 (A) δ 8.55 (bs, 1H), 6.95-7.75 (m, 9H), 5.07 and 4.93 (bs, 2H), 4.53 and 4.48 (bs, 2H), 4.09 and 4.05 (d, J = 17.1 Hz, 1H), 3.70 and 3.66 (d, J = 17.4 Hz, 1H), 3.47 and 3.14 (s, 3H), 2.38 and 2.33 (s, 3H). 6-028 (B) δ 8.5-8.6 (m, 1H), 7.6-7.75 (m, 1H), 7.05-7.55 (m, 8H), 3.25-5.2 (m, 8H), 3.37 and 3.17 (s, 3H), 2.28 and 2.34 (s, 3H). 6-029 (A) δ 8.5-8.6 (m, 1H), 6.95-7.75 (m, 9H), 4.98 (bs, 2H), 4.58 and 4.37 (bs, 2H), 4.09 and 4.05 (d, J = 17.2 Hz, 1H), 3.70 and 3.67 (d, J = 17.2 Hz, 1H), 2.38 and 2.31 (s, 3H), 2.29 and 1.99 (s, 3H). 6-030 (B) δ 8.5-8.65 (m, 1H), 7.15-7.8 (m, 8H), 7.0-7.05 (m, 1H), 3.5-5.3 (m, 6H), 3.77 and 3.65 (s, 3H), 2.45 and 2.32 (s, 3H). 6-031 (B) δ 8.5-8.65 (m, 1H), 7.2-7.8 (m, 8H), 6.9-7.0 (m, 1H), 4.0-5.2 (m, 5H), 3.6-3.8 (m, 1H), 2.35 (s, 3H). 6-032 (B) δ 8.5-8.65 (m, 1H), 7.0-7.8 (m, 9H), 5.8-6.0 and 5.55-5.75 (m, 1H), 3.6-5.55 (m, 8H), 2.37 and 2.34 (s, 3H). 6-033 (B) δ 8.5-8.65 (m, 1H), 7.05-7.75 (m, 9H), 3.5-5.3 (m, 6H), 2.37 (s, 3H), 2.28 (s, 1H). 6-034 (B) δ 8.45-8.5 (m, 1H), 7.6-7.65 (m, 1H), 7.4-7.55 (m, 6H), 7.15-7.2 (m, 2H), 4.98 (s, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.39 (s, 3H). 6-035 (A) δ 8.45-8.55 (m, 1H), 7.6-7.7 (m, 1H), 7.35-7.55 (m, 6H), 7.1-7.25 (m, 2H), 4.99 (s, 2H), 4.06 (d, J = 19.0 Hz, 1H), 3.67 (d, J = 19.0 Hz, 1H), 2.74 (q, J = 8.2 Hz, 2H), 2.39 (s, 3H), 1.11 (t, J = 8.2 Hz, 3H). 6-036 (A) δ 8.49 (d, J = 4.8 Hz, 1H), 7.63 (td, J = 7.8, 1.8 Hz, 1H), 7.35-7.55 (m, 6H), 7.1-7.2 (m, 2H), 4.98 (s, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.70 (t, J = 7.2 Hz, 2H), 1.64 (hex, J = 7.2 Hz, 2H), 1.55 (s, 3H), 0.89 (t, J = 7.2 Hz, 3H). 6-037 (A) δ 8.49 (d, J = 5.1 Hz, 1H), 7.63 (td, J = 7.8, 1.8 Hz, 1H), 7.35-7.55 (m, 6H), 7.1-7.25 (m, 2H), 4.99 (s, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz, 1H), 3.1-3.3 (m, 1H), 2.42 (s, 3H), 1.13 (d, J = 6.6 Hz, 6H). 6-038 (A) δ 8.53 (d, J = 4.8 Hz, 1H), 7.64 (td, J = 7.8, 1.8 Hz, 1H), 7.45-7.55 (m, 5H), 7.4-7.45 (m, 1H), 7.15-7.3 (m, 2H), 5.16 (s, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H), 1.9-2.0 (m, 1H), 0.95-1.05 (m, 2H), 0.7-0.8 (m, 2H). 6-039 (A) δ 8.50 (d, J = 5.2 Hz, 1H), 7.55-7.65 (m, 1H), 7.4-7.55 (m, 6H), 7.1-7.2 (m, 2H), 4.86 (s, 2H), 4.06 (d, J = 19.0 Hz, 1H), 3.68 (d, J = 19.0 Hz, 1H), 2.44 (s, 3H), 1.34 (s, 9H). 6-041 (B) δ 8.5-8.55 (m, 1H), 7.6-7.7 (m, 1H), 7.4-7.55 (m, 6H), 7.27 (s, 1H), 7.15-7.2 (m, 1H), 6.47 (dd, J = 16.0, 10.0 Hz, 1H), 6.30 (d, J = 16.0 Hz, 1H), 5.62 (d, J = 10.0 Hz, 1H), 5.10 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H). 6-042 (A) δ 8.54 (d, J = 0.9 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.15-7.75 (m, 13H), 5.32 (s, 2H), 3.95 (d, J = 19.0 Hz, 1H), 3.58 (d, J = 19.0 Hz, 1H), 2.34 (s, 3H). 6-043 (A) δ 8.56 (d, J = 4.8 Hz, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.21 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.58 (s, 3H), 2.40 (s, 3H). 6-044 (A) δ 8.56 (d, J = 3.9 Hz, 1H), 7.65 (td, J = 7.8, 1.8 Hz, 1H), 7.35-7.55 (m, 6H), 7.15-7.3 (m, 2H), 5.21 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 4.00 (q, J = 7.2 Hz, 2H), 3.69 (d, J = 17.4 Hz, 1H), 2.41 (s, 3H), 0.92 (t, J = 7.2 Hz, 3H). 6-045 (A) δ 8.55 (d, J = 4.8 Hz, 1H), 7.67 (td, J = 7.8, 1.8 Hz, 1H), 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.20 (s, 2H), 4.7-4.85 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H), 0.91 (d, J = 6.3 Hz, 6H). 6-046 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H), 5.23 (s, 2H), 4.17 (d, J = 17.0 Hz, 1H), 3.75 (d, J = 6.8 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 2.42 (s, 3H), 1.55-1.65 (m, 1H), 0.64 (d, J = 6.8 Hz, 6H). 6-047 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.23 (s, 2H), 4.15-4.25 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.3-3.4 (m, 2H), 2.42 (s, 3H). 6-048 (B) δ 8.55-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.23 (s, 2H), 4.05-4.15 (m, 3H), 3.69 (d, J = 17.0 Hz, 1H), 3.2-3.25 (m, 2H), 3.15 (s, 3H), 2.49 (s, 3H). 6-049 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H), 5.45-5.6 (m, 1H), 5.23 (s, 2H), 5.0-5.1 (m, 2H), 4.4-4.45 (m, 2H), 4.18 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H). 6-050 (B) δ 8.54 (d, J = 4.8 Hz, 1H), 7.6-7.7 (m, 1H), 7.35-7.55 (m, 6H), 7.15-7.25 (m, 2H), 5.13 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H), 2.27 (s, 3H). 6-051 (B) δ 8.55-8.6 (m, 1H), 7.6-7.65 (m, 1H), 7.45-7.5 (m, 5H), 7.35-7.4 (m, 1H), 7.2-7.25 (m, 1H), 7.0-7.05 (m, 1H), 4.96 (s, 2H), 4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.0 Hz, 1H), 3.43 (s, 3H), 2.37 (s, 3H). 6-053 (B) δ 8.65-8.7 (m, 1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m, 2H), 7.3-7.45 (m, 5H), 5.17 (s, 2H), 4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.0 Hz, 1H), 3.50 (s, 6H), 2.46 (s, 3H). 6-054 (B) δ 8.4-8.45 (m, 1H), 7.8-7.85 (m, 1H), 7.2-7.6 (m, 7H), 4.2-5.3 (m, 2H), 4.05-4.15 (m, 1H), 3.65-3.75 (m, 1H), 3.05-3.15 (m, 2H), 2.34 and 2.29 (s, 3H), 1.25-1.3 and 1.0-1.1 (m, 3H). 6-055 (A) δ 8.6-8.65 (m, 2H), 7.5-7.55 (m, 4H), 7.43 (s, 1H), 7.25-7.3 (m, 3H), 4.76 (s, 2H), 4.11 (d, J = 19.0 Hz, 1H), 3.71 (d, J = 19.0 Hz, 1H), 2.45-2.5 (m, 1H), 2.34 (s, 3H), 1.2-1.3 (m, 4H). 6-056 (A) δ 8.6-8.75 (m, 2H), 7.4-7.6 (m, 6H), 7.15-7.25 (m, 1H), 5.12 (s, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.69 (q, J = 7.9 Hz, 2H), 2.43 (s, 3H), 1.11 (t, J = 7.9 Hz, 3H). 6-069 (B) δ 7.8-7.9 (m, 2H), 7.67 (d, J = 7.6 Hz, 1H), 7.51 (bs, 2H), 7.4-7.45 (m, 1H), 4.42 (s, 2H), 4.13 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz, 1H), 3.22 (s, 3H). 6-070 (A) δ 8.55 (d, J = 4.4 Hz, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.81 (s, 1H), 7.15-7.7 (m, 7H), 4.93 (s, 2H), 4.52 (s, 2H), 4.13 (d, J = 17.0 Hz, 1H), 3.76 (d, J = 17.0 Hz, 1H). 6-073 (A) δ 8.55 (d, J = 4.7 Hz, 1H), 8.37 (bs, 1H), 8.02 (d, J = 8.5 Hz, 1H), 7.91 (d, J = 8.5 Hz, 1H), 7.83 (bs, 1H), 7.69 (t, J = 7.7 Hz, 1H), 7.52 (bs, 2H), 7.4-7.5 (m, 2H), 7.15-7.3 (m, 1H), 5.27 (s, 2H), 4.15 (d, J = 17.3 Hz, 1H), 3.77 (d, J = 17.3 Hz, 1H). 6-074 (B) δ 7.5-7.7 (m, 4H), 7.43 (s, 1H), 7.35-7.4 (m, 1H), 4.50 (q, J = 8.4 Hz, 2H), 4.16 (d, J = 17.0 Hz, 1H), 3.75 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H), 2.15 (s, 3H). 6-075 (B) δ 7.7-7.8 (m, 3H), 7.55-7.65 (m, 2H), 7.35-7.4 (m, 1H), 4.50 (q, J = 8.6 Hz, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H), 2.16 (s, 3H). 6-076 (B) δ 8.45-8.5 (m, 2H), 7.7-7.75 (m, 2H), 7.6-7.65 (m, 1H), 7.69 (s, 1H), 7.4-7.45 (m, 2H), 7.15-7.2 (m, 2H), 4.97 (s, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.40 (s, 3H). 6-077 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.23 (d, J = 7.9 Hz, 1H), 4.62 (q, J = 8.4 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.67 (s, 3H), 2.36 (s, 3H). 6-078 (A) δ 8.79 and 8.75 (d, J = 1.8 Hz, 1H), 7.3-7.55 (m, 7H), 4.85-5.2 (m, 2H), 4.53 and 4.50 (bs, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 3.47 and 3.14 (s, 3H), 2.36 and 2.25 (s, 3H). 6-079 (A) δ 8.55 and 8.53 (d, J = 4.8 Hz, 1H), 7.69 and 7.59 (td, J = 7.8, 1.8 Hz, 1H), 7.25-7.55 (m, 8H), 4.8-5.25 (m, 2H), 4.57 and 4.49 (bs, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 3.65 and 3.27 (q, J = 6.9 Hz, 2H), 2.37 and 2.34 (s, 3H), 1.26 and 1.08 (t, J = 6.9 Hz, 3H). 6-080 (B) δ 8.58 (ddd, J = 4.9, 1.8, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H), 7.35-7.55 (m, 7H), 7.18 (dd, J = 7.5, 4.9 Hz, 1H), 5.98 (q, J = 7.1 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.42 (s, 3H), 2.43 (s, 3H), 1.90 (d, J = 7.0 Hz, 3H). 6-081 (A) δ 8.21 (d, J = 4.2 Hz, 1H), 7.3-7.6 (m, 7H), 6.80 (dd, J = 8.1, 4.2 Hz, 1H), 6.60 (d, J = 8.7 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.66 (d, J = 17.1 Hz, 1H), 3.34 (s, 3H), 2.45 (s, 3H), 2.42 (s, 3H). 6-082 (A) δ 8.22 (d, J = 4.8 Hz, 1H), 7.4-7.65 (m, 7H), 6.78 (dd, J = 7.2, 4.8 Hz, 1H), 6.63 (d, J = 8.4 Hz, 1H), 4.08 (d, J = 16.8 Hz, 1H), 3.70 (s, 3H), 3.69 (d, J = 16.8 Hz, 1H), 3.40 (s, 3H), 2.46 (s, 3H). 6-083 (A) δ 8.42 (s, 2H), 7.35-7.55 (m, 6H), 6.77 (t, J = 5.1 Hz, 1H), 4.06 (d, J = 18.1 Hz, 1H), 3.67 (d, J = 18.1 Hz, 1H), 3.43 (s, 3H), 2.44 (s, 3H), 2.43 (s, 3H). 6-084 (A) δ 8.46 (bs, 1H), 8.40 (bs, 1H), 7.45-7.6 (m, 5H), 7.43 (s, 1H), 6.74 (t, J = 4.8 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.69 (s, 3H), 3.53 (s, 3H), 2.46 (s, 3H). 6-085 (B) δ 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 3.85-4.2 (m, 3H), 3.6-3.8 (m, 1H), 2.5-2.65 (m, 2H), 2.32 and 2.30 (s, 3H), 2.1-2.2 (m, 2H). 6-086 (A) δ 7.4-7.6 (m, 6H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.89 (s, 4H), 2.57 (s, 3H). 6-089 (B) δ 7.45-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.2-7.3 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.13 (bs, 3H), 2.7-2.8 (m, 2H), 2.37 (bs, 3H), 1.15 (m, 3H). 6-092 (B) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 1H), 7.33 (d, J = 8.0 Hz, 1H), 5.10 (s, 2H), 4.50 (s, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.6-3.75 (m, 3H), 3.27 (q, J = 6.8 Hz, 2H), 2.36 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H), 1.10 (t, J = 7.0 Hz, 3H). 6-093 (A) δ 7.5-7.7 (m, 4H), 7.44 (t, J = 2.0 Hz, 1H), 7.35 (d, J = 7.6 Hz, 1H), 5.03 (s, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.50 (q, J = 7.0 Hz, 2H), 2.48 (s, 3H), 2.40 (s, 3H), 1.15 (t, J = 7.0 Hz, 3H). 6-094 (A) δ 7.5-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.2-7.3 (m, 1H), 5.14 and 4.62 (s, 2H), 4.05-4.15 (m, 2H), 3.6-3.75 (m, 2H), 3.20 and 2.87 (s, 3H), 2.33 and 2.35 (s, 3H). 6-095 (B) δ 7.3-7.6 (m, 6H), 5.15 (s, 2H), 3.95-4.2 (m, 3H), 3.71 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H), 2.40 (s, 3H). 6-096 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.24 (d, J = 8.1 Hz, 1H), 4.12 (t, J = 5.5 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.66 (t, J = 5.5 Hz, 2H), 3.61 (s, 3H), 3.37 (s, 3H), 2.36 (s, 3H). 6-097 (A) δ 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 5.18 and 4.87 (t, J = 4.6 Hz, 1H), 3.65-4.2 (m, 8H), 3.20 and 2.89 (s, 3H), 2.34 and 2.32 (s, 3H). 6-098 (A) δ 7.5-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 7.8 Hz, 1H), 5.12 (t, J = 4.6 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.8-3.95 (m, 6H), 3.70 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H), 2.33 (s, 3H). 6-099 (A) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.25-7.3 (m, 1H), 5.32 (t, J = 4.6 Hz, 1H), 3.9-4.15 (m, 7H), 3.69 (d, J = 17.4 Hz, 1H), 3.62 (s, 3H), 2.38 (s, 3H). 6-100 (A) δ 7.4-7.65 (m, 6H), 5.72 (dd, J = 7.2, 5.7 Hz, 1H), 4.10 (d, J = 17.1 Hz, 1H), 4.0-4.15 (m, 1H), 3.75-3.85 (m, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H), 2.3-2.45 (m, 1H), 2.22 (s, 3H), 2.1-2.25 (m, 2H), 1.8-1.95 (m, 1H). 6-101 (A) δ 7.35-7.6 (m, 5H), 6.6-7.3 (m, 2H), 3.65-4.45 (m, 7H), 3.13 and 2.82 (d, J = 7.8 Hz, 3H), 2.3-2.35 (m, 3H). 6-102 (A) δ 6.6-7.6 (m, 7H), 4.35-4.45 (m, 2H), 3.65-4.15 (m, 5H), 2.3-2.45 (m, 6H). 6-103 (A) δ 6.65-7.55 (m, 7H), 4.6-4.75 (m, 2H), 3.6-4.15 (m, 8H), 2.37 and 2.35 (s, 3H). 6-105 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 8.8 Hz, 2H), 7.14 (d, J = 8.1 Hz, 1H), 6.87 (d, J = 8.8 Hz, 2H), 5.00 (s, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.81 (s, 3H), 3.68 (d, J = 17.2 Hz, 1H), 3.58 (s, 3H), 2.29 (s, 3H). 6-106 (B) δ 8.22 (d, J = 8.7 Hz, 2H), 7.59 (d, J = 8.7 Hz, 2H), 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.18 (d, J = 7.9 Hz, 1H), 5.15 (s, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.58 (s, 3H), 2.16 (s, 3H). 6-107 (B) δ 7.3-7.6 (m, 14H), 7.19 (d, J = 8.1 Hz, 1H), 5.11 (s, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H), 3.60 (s, 3H), 2.37 (s, 3H). 6-108 (A) δ 7.81 (bs, 1H), 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 6.56 (s, 1H), 6.13 (s, 2H), 4.07 (d, J = 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.28 (s, 3H), 1.23 (s, 9H). 6-109 (B) δ 8.08 (dt, J = 7.5, 0.9 Hz, 1H), 7.89 (dt, J = 8.4, 0.9 Hz, 1H), 7.4-7.6 (m, 7H), 7.14 (d, J = 8.1 Hz, 1H), 6.72 (s, 2H), 4.06 (d, J = 17.2 Hz, 1H), 3.69 (s, 3H), 3.68 (d, J = 17.2 Hz, 1H), 2.25 (s, 3H). 6-111 (A) δ 8.56 (d, J = 4.2 Hz, 1H), 6.7-7.85 (m, 13H), 5.21 (s, 2H), 4.00 (d, J = 17.4 Hz, 1H), 3.60 (d, J = 17.4 Hz, 1H), 2.40 (s, 3H). 6-112 (A) δ 8.72 (d, J = 4.8 Hz, 2H), 7.4-7.6 (m, 6H), 7.22 (t, J = 4.8 Hz, 1H), 5.33 (s, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 3.58 (s, 3H), 2.44 (s, 3H). 6-113 (B) δ 7.82 (t, J = 6.0 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (bs, 1H), 7.2-7.3 (m, 1H), 4.8-4.85 (m, 1H), 3.65-4.15 (m, 4H), 3.15-3.25 (m, 2H), 2.5-2.6 (m, 1H), 2.34 (s, 3H), 1.85-2.1 (m, 3H). 6-114 (A) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 2.0 Hz, 1H), 7.25-7.35 (m, 1H), 5.19 (s, 1H), 4.59 (s, 1H), 4.0-4.2 (m, 3H), 3.65-3.8 (m, 2H), 3.27 (t, J = 6.4 Hz, 1H), 2.39 (bs, 3H). 6-115 (A) δ 7.4-7.6 (m, 5H), 7.25-7.35 (m, 1H), 4.77 (s, 1H), 4.0-4.2 (m, 3H), 3.70 (d, J = 17.4 Hz, 1H), 3.45 (t, J = 6.4 Hz, 1H), 3.13 (t, J = 6.4 Hz, 1H), 2.97 (t, J = 6.4 Hz, 1H), 2.36 (m, 3H). 6-119 (A) δ 7.4-7.55 (m, 6H), 4.08 (d, J = 17.4 Hz, 1H), 3.8-3.85 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H), 3.2-3.25 (m, 2H), 2.45-2.5 (m, 2H), 2.2-2.35 (m, 8H). 6-120 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.30 (d, J = 7.9 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.89 (s, 3H), 3.82 (s, 3H), 3.69 (d, J = 17.2 Hz, 1H), 2.38 (s, 3H). 6-121 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.77 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H), 2.84 (s, 6H), 2.40 (s, 3H). 6-122 (B) δ 8.0-8.15 (m, 1H), 7.4-7.6 (m, 5H), 4.11 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.68 (s, 3H), 2.33 (s, 6H). 6-123 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.31 (d, J = 7.9 Hz, 1H), 4.8-4.9 (m, 1H), 4.76 (ddd, J = 47.6, 11.0, 2.4 Hz, 1H), 4.58 (ddd, J = 46.0, 11.0, 2.7 Hz, 1H), 4.28 (dd, J = 11.2, 10.0 Hz, 1H), 4.18 (dd, J = 11.2, 5.5 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.35 (s, 3H). 6-124 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.34 (d, J = 8.6 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.75 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H), 3.14 (bs, 3H), 3.07 (bs, 3H), 2.44 (s, 3H). 6-125 (B) δ 9.12 (t, J = 7.3 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H), 3.39 (tq, J = 7.3, 7.1 Hz, 2H), 3.01 (s, 3H), 2.37 (s, 3H), 1.24 (t, J = 7.1 Hz, 3H). 6-126 (B) δ 9.65 (t, J = 6.2 Hz, 1H), 7.15-7.65 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.29 (d, J = 7.9 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95-4.1 (m, 2H), 3.71 (d, J = 17.2 Hz, 1H), 3.07 (s, 3H), 2.36 (s, 3H). 6-130 (A) δ 7.2-7.7 (m, 6H), 6.15 (s, 1H), 5.15-5.35 (m, 1H), 4.5-4.8 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.6-4.3 (m, 3H), 3.48 and 3.03 (s, 3H), 2.36 and 2.34 (s, 3H), 1.7-2.45 (m, 4H). 6-131 (A) δ 7.35-7.6 (m, 6H), 5.65-5.75 (m, 1H), 4.05-4.2 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.7-3.85 (m, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.51 (q, J = 6.0 Hz, 2H), 2.49 (s, 3H), 1.6-2.6 (m, 4H), 1.08 (t, J = 6.0 Hz, 3H). 6-132 (A) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 2H), 5.78 (t, J = 6.3 Hz, 1H), 4.05-4.15 (m, 2H), 3.75-3.85 (m, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.7-2.9 (m, 1H), 2.50 (s, 3H), 2.25-2.4 (m, 1H), 2.1-2.25 (m, 2H), 1.8-1.95 (m, 1H), 1.06 and 1.08 (d, J = 6.0 Hz, 6H). 7-002 (A) δ 7.87 (bs, 1H), 7.78 (d, J = 8.1 Hz, 2H), 7.65 (d, J = 8.1 Hz, 2H), 7.50 (bs, 2H), 7.43 (bs, 1H), 4.55-4.7 (m, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H). 7-003 (A) δ 8.85 (s, 1H), 8.49 (bs, 1H), 7.86 (d, J = 8.4 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H), 7.43 (d, J = 1.8 Hz, 1H), 7.40 (s, 1H), 5.13 (d, J = 4.8 Hz, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.1 Hz, 1H). 7-008 (A) δ 8.79 (s, 1H), 8.14 (bs, 1H), 7.35-7.5 (m, 7H), 5.11 (d, J = 5.0 Hz, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.1 Hz, 1H), 2.37 (s, 3H). 7-009 (A) δ 9.06 (bs, 1H), 8.50 (d, J = 4.5 Hz, 1H), 7.75 (t, J = 7.2 Hz, 1H), 7.2-7.6 (m, 8H), 5.04 (d, J = 4.2 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H). 8-001 (A) δ 8.40 (d, J = 8.2 Hz, 2H), 7.74 (d, J = 8.2 Hz, 2H), 7.53 (s, 2H), 7.43 (s, 1H), 7.04 (d, J = 4.7 Hz, 1H), 6.74 (d, J = 4.7 Hz, 1H), 4.13 (d, J = 17.3 Hz, 1H), 3.89 (s, 3H), 3.74 (d, J = 17.3 Hz, 1H). 8-002 (A) δ 8.22 (d, J = 8.0 Hz, 2H), 7.56 (s, 1H), 7.53 (s, 2H), 7.43 (s, 1H), 7.03 (d, J = 4.7 Hz, 1H), 6.72 (d, J = 4.7 Hz, 1H), 4.12 (d, J = 17.3 Hz, 1H), 3.84 (s, 3H), 3.72 (d, J = 17.3 Hz, 1H), 2.74 (s, 3H). 8-003 (A) δ 8.19 (d, J = 8.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (s, 1H), 7.04 (d, J = 4.8 Hz, 1H), 6.71 (d, J = 4.8 Hz, 1H), 4.23 (t, J = 7.2 Hz, 2H), 4.12 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.73 (s, 3H), 1.91 (hex, J = 7.2 Hz, 2H), 0.99 (t, J = 7.2 Hz, 3H). 8-004 (A) δ 8.17 (d, J = 8.1 Hz, 1H), 7.45-7.65 (m, 4H), 7.41 (s, 1H), 7.36 (t, J = 4.2 Hz, 1H), 4.12 (d, J = 17.4 Hz, 1H), 3.79 (s, 3H), 3.74 (d, J = 17.4 Hz, 1H), 3.17 (d, J = 4.2 Hz, 2H), 2.69 (s, 3H). 8-005 (A) δ 8.50 (s, 1H), 7.95 (d, J = 7.8 Hz, 1H), 7.68 (d, J = 6.6 Hz, 1H), 7.4-7.6 (m, 5H), 6.32 (dd, J = 6.6, 4.2 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.67 (s, 3H), 2.68 (s, 3H). 8-006 (A) δ 8.97 (s, 1H), 7.3-7.7 (m, 6H), 4.12 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 3.62 (s, 3H), 2.36 (s, 3H). 8-007 (A) δ 8.58 (d, J = 9.9 Hz, 1H), 8.08 (d, J = 7.8 Hz, 1H), 7.4-7.6 (m, 5H), 7.30 (d, J = 9.9 Hz, 1H), 4.11 (d, J = 17.1 Hz, 1H), 4.00 (s, 3H), 3.72 (d, J = 17.1 Hz, 1H), 2.67 (s, 3H). 9-003 (B) δ 8.75 (d, J = 1.2 Hz, 1H), 8.7-8.75 (m, 1H), 8.14 (t, J = 1.8 Hz, 1H), 7.5-7.6 (m, 2H), 7.45 (d, J = 8.6 Hz, 1H), 6.0-6.05 (m, 1H), 4.05-4.2 (m, 3H), 3.74 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 9-008 (A) δ 7.97 (s, 1H), 7.45-7.55 (m, 2H), 7.35-7.4 (m, 1H), 6.44 (t, J = 6.3 Hz, 1H), 4.40 (d, J = 17.6 Hz, 1H), 4.0-4.15 (m, 3H), 2.42 (s, 3H). 9-009 (A) δ 8.51 (dd, J = 5.1, 0.9 Hz, 1H), 7.96 (s, 1H), 7.70 (td, J = 7.5, 1.5 Hz, 1H), 7.5-7.6 (m, 3H), 7.3-7.4 (m, 2H), 7.15-7.25 (m, 1H), 4.74 (d, J = 4.8 Hz, 2H), 4.40 (d, J = 17.6 Hz, 1H), 4.09 (d, J = 17.6 Hz, 1H), 2.50 (s, 3H). 9-010 (B) δ 7.45-7.55 (m, 2H), 7.40 (d, J = 7.9 Hz, 1H), 7.04 (d, J = 4.0 Hz, 1H), 6.89 (d, J = 4.0 Hz, 1H), 6.25 (bs, 1H), 4.05-4.15 (m, 2H), 4.03 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H). 9-011 (B) δ 8.5-8.55 (m, 1H), 7.70 (td, J = 7.5, 1.8 Hz, 1H), 7.45-7.65 (m, 3H), 7.43 (t, J = 5.1 Hz, 1H), 7.34 (d, J = 7.9 Hz, 1H), 7.15-7.25 (m, 1H), 7.04 (d, J = 3.8 Hz, 1H), 6.88 (d, J = 4.0 Hz, 1H), 4.73 (d, J = 5.0 Hz, 2H), 4.04 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 10-001  (A) δ 8.87 (d, J = 2.1 Hz, 1H), 8.25-8.3 (m, 2H), 8.14 (dd, J = 8.1, 2.1 Hz, 1H), 7.51 (bs, 2H), 7.45 (d, J = 1.8 Hz, 1H), 4.05-4.2 (m, 3H), 3.75 (d, J = 17.4 Hz, 1H). 10-002  (A) δ 8.94 (bs, 1H), 8.88 (bs, 1H), 8.61 (d, J = 5.1 Hz, 1H), 8.30 (d, J = 7.8 Hz, 1H), 8.12 (dd, J = 8.1, 2.1 Hz, 1H), 7.68 (td, J = 7.8, 1.8 Hz, 1H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H), 7.34 (d, J = 7.8 Hz, 1H), 7.2-7.25 (m, 1H), 4.80 (d, J = 5.4 Hz, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 10-003  (A) δ 8.53 (d, J = 1.8 Hz, 1H), 8.48 (d, J = 8.4 Hz, 1H), 7.74 (dd, J = 8.4, 1.8 Hz, 1H), 7.47 (bs, 3H), 4.0-4.2 (m, 2H), 4.05 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H). 10-004  (A) δ 9.01 (s, 1H), 8.17 (d, J = 8.4 Hz, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 6.77 (t, J = 6.3 Hz, 1H), 4.26 (d, J = 18.3 Hz, 1H), 4.05-4.25 (m, 2H), 3.89 (d, J = 18.3 Hz, 1H). 10-005  (A) δ 9.09 (s, 1H), 8.57 (d, J = 5.1 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 8.12 (d, J = 8.4 Hz, 1H), 7.86 (bs, 1H), 7.65-7.75 (m, 1H), 7.52 (s, 2H), 7.43 (s, 1H), 7.2-7.35 (m, 2H), 4.78 (d, J = 4.2 Hz, 2H), 4.28 (d, J = 18.3 Hz, 1H), 3.90 (d, J = 18.3 Hz, 1H). 11-034  (A) δ 7.96 (t, J = 7.0 Hz, 1H), 7.88 (dd, J = 8.2, 1.6 Hz, 1H), 7.81 (dd, J = 11.8, 1.4 Hz, 1H), 7.51 (bs, 2H), 7.4-7.45 (m, 1H), 4.20 (dd, J = 18.2, 1.4 Hz, 1H), 3.82 (d, J = 18.2 Hz, 1H). 11-038  (A) δ 7.89 (d, J = 8.1 Hz, 1H), 7.72 (s, 1H), 7.64 (d, J = 8.1 Hz, 1H), 7.50 (s, 2H), 7.43 (s, 1H), 4.09 (d, J = 17.1 Hz, 1H), 3.95 (s, 3H), 3.71 (d, J = 17.1 Hz, 1H). 11-056  (A) δ 8.64 (d, J = 4.5 Hz, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.75 (td, J = 7.7, 1.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.35-7.45 (m, 2H), 7.28 (t, J = 6.2 Hz, 1H), 5.48 (s, 2H), 4.11 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.65 (s, 3H). 11-057  (B) δ 8.4-8.45 (m, 1H), 7.75 (s, 1H), 7.5-7.65 (m, 5H), 7.44 (s, 1H), 6.55 (s, 1H), 4.12 (d, J = 17.0 Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H), 2.37 (s, 3H). 11-059  (A) δ 7.90 (d, J = 8.4 Hz, 1H), 7.4-7.7 (m, 5H), 4.11 (d, J = 17.4 Hz, 1H), 3.91 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H), 3.50 (q, J = 7.5 Hz, 2H), 1.25 (t, J = 7.5 Hz, 3H). 11-060  (A) δ 8.02 (d, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.67 (d, J = 6.3 Hz, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 4.95 (s, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.97 (s, 3H), 3.74 (d, J = 17.4 Hz, 1H). 11-062  (B) δ 8.07 (t, J = 0.8 Hz, 1H), 7.99 (ddd, J = 8.0, 1.6, 0.4 Hz, 1H), 7.93 (dd, J = 7.4, 0.6 Hz, 1H), 7.48-7.52 (m, 2H), 7.46 (t, J = 1.4 Hz, 1H), 4.11 (d, J = 16.8 Hz, 1H), 3.74 (dd, J = 17.4, 1.0 Hz, 1H). 11-063  (B) δ 8.00 (s, 1H), 7.93 (d, J = 8.1 Hz, 1H), 7.87 (d, J = 8.1 Hz, 1H), 7.51 (s, 2H), 7.4-7.5 (m, 1H), 4.12 (d, J = 16.7 Hz, 1H), 3.96 (s, 3H), 3.74 (d, J = 16.7 Hz, 1H). 11-071  (B) δ 8.03 (d, J = 8.0 Hz, 1H), 7.6-7.7 (m, 2H), 7.51 (s, 2H), 7.4-7.5 (m, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95 (s, 3H), 3.70 (d, J = 17.2z, 1H). 11-073  (A) δ 7.95-8.05 (m, 1H), 7.4-7.5 (m, 2H), 7.2-7.35 (m, 3H), 4.06 (d, J = 17.1 Hz, 1H), 3.95 (s, 3H), 3.70 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H). 11-092  (A) δ 7.94 (d, J = 8.8 Hz, 1H), 7.4-7.6 (m, 5H), 4.37 (q, J = 7.1 Hz, 2H), 4.15 (d, J = 17.3 Hz, 1H), 3.73 (d, J = 17.3 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J = 7.1 Hz, 3H). 11-095  (A) δ 7.94 (d, J = 8.8 Hz, 1H), 7.5-7.8 (m, 5H), 4.37 (q, J = 7.1 Hz, 2H), 4.09 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J = 7.1 Hz, 3H). 11-102  (A) δ 7.85-7.95 (m, 1H), 7.35-7.6 (m, 5H), 6.91 (s, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H). 11-105  (A) δ 8.06 (d, J = 8.4 Hz, 1H), 7.68 (dd, J = 8.4, 1.8 Hz, 1H), 7.62 (d, J = 1.8 Hz, 1H), 7.50 (d, J = 1.5 Hz, 2H), 7.43 (t, J = 1.5 Hz, 1H), 7.08 (s, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H). 11-107  (A) δ 7.68 (d, J = 1.8 Hz, 1H), 7.58 (dd, J = 8.1, 1.8 Hz, 1H), 7.45-7.55 (m, 3H), 7.43 (t, J = 1.8 Hz, 1H), 5.22 (s, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.15 (s, 3H). 11-112  (A) δ 8.08 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 1.8 Hz, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.49 (d, J = 1.5 Hz, 2H), 7.44 (t, J = 1.5 Hz, 1H), 7.04 (s, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H). 11-113  (A) δ 7.84 (s, 1H), 7.55-7.7 (m, 2H), 7.50 (d, J = 1.5 Hz, 2H), 7.43 (t, J = 1.5 Hz, 1H), 4.77 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H). 11-114  (A) δ 7.86 (s, 1H), 7.63 (d, J = 8.1 Hz, 1H), 7.4-7.55 (m, 4H), 4.20 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.17 (s, 3H). 11-116  (A) δ 10.07 (s, 1H), 8.23 (s, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.50 (s, 2H), 7.44 (s, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H). 11-118  (A) δ 7.5-7.55 (m, 3H), 7.48 (dd, J = 8.1, 1.8 Hz, 1H), 7.42 (t, J = 1.8 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 4.60 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H). 11-119  (A) δ 7.45-7.55 (m, 3H), 7.47 (s, 2H), 7.42 (s, 1H), 4.74 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.36 (s, 3H). 11-122  (A) δ 9.35 (s, 1H), 7.4-7.45 (m, 5H), 7.2-7.3 (m, 1H), 4.39 (q, J = 7.1 Hz, 2H), 4.21 (d, J = 17.3 Hz, 1H), 3.83 (d, J = 17.3 Hz, 1H), 1.40 (t, J = 7.1 Hz, 3H). 11-125  (A) δ 7.45-8.05 (m, 6H), 6.66 (t, J = 72.3 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H). 11-126  (A) δ 6.7-7.5 (m, 6H), 6.50 (t, J = 74.1 Hz, 1H), 4.23 (bs, 2H), 4.02 (d, J = 17.4 Hz, 1H), 3.63 (d, J = 17.4 Hz, 1H). 11-127  (A) δ 7.2-7.95 (m, 6H), 6.57 (t, J = 73.2 Hz, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H). 11-129  (A) δ 7.95 (q, J = 8.7 Hz, 1H), 7.66 (s, 1H), 7.5-7.6 (m, 4H), 4.37 (q, J = 7.2 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J = 7.2 Hz, 3H). 11-130  (A) δ 8.09 (s, 2H), 7.95-8.0 (m, 2H), 7.5-7.6 (m, 2H), 4.38 (q, J = 7.2 Hz, 2H), 4.21 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H), 2.63 (s, 3H), 1.41 (t, J = 7.2 Hz, 3H). 14-004  (A) δ 7.40 (s, 1H), 7.35 (s, 2H), 5.99 (s, 1H), 5.65 (s, 1H). 14-005  (B) δ 7.2-7.45 (m, 3H), 6.10 (s, 1H), 5.92 (s, 1H). 14-006  (A) δ 7.40 (s, 2H), 7.33 (s, 1H), 5.63 (s, 1H), 5.45 (s, 1H), 4.47 (s, 2H), 3.84 (q, J = 8.8 Hz, 2H). 14-007  (B) δ 7.3-7.4 (m, 3H), 5.22 (s, 1H), 5.02 (s, 1H), 2.07 (s, 2H), 0.04 (s, 9H). 14-008  (A) δ 8.63 (d, J = 5.1 Hz, 1H), 7.69 (t, J = 8.0 Hz, 1H), 7.2-7.4 (m, 5H), 5.99 (s, 1H), 5.64 (s, 1H). 14-009  (A) δ 7.25-7.6 (m, 3H), 6.04 (s, 1H), 5.80 (s, 1H). 14-010  (B) δ 7.24 (s, 1H), 7.20 (s, 1H), 7.14 (s, 1H), 5.97 (s, 1H), 5.77 (s, 1H), 2.36 (s, 3H). 14-012  (A) δ 7.40 (d, J = 6.3 Hz, 2H), 6.04 (s, 1H), 5.79 (s, 1H). 14-013  (B) δ 7.54 (s, 2H), 6.06 (s, 1H), 5.83 (s, 1H). 14-016  (A) δ 7.70 (s, 1H), 7.52 (s, 2H), 6.04 (s, 1H), 5.80 (s, 1H). 14-018  (A) δ 7.65 (s, 1H), 7.62 (s, 1H), 7.58 (s, 1H), 6.11 (s, 1H), 5.87 (s, 1H). 14-020  (A) δ 7.69 (d, J = 6.3 Hz, 1H), 7.58 (d, J = 5.7 Hz, 1H), 6.10 (s, 1H), 5.83 (s, 1H). 14-021  (A) δ 7.2-7.45 (m, 4H), 5.98 (s, 1H), 5.78 (s, 1H), 2.93 (dd, J = 10.8, 7.8 Hz, 1H), 2.01 (dd, J = 10.8, 7.8 Hz, 1H), 1.87 (t, J = 7.8 Hz, 1H). 14-022  (B) δ 7.35-7.45 (m, 2H), 7.2-7.3 (m, 2H), 6.09 (d, J = 53.2 Hz, 1H), 6.03 (s, 1H), 5.82 (s, 1H). 14-023  (B) δ 7.2-7.5 (m, 6H), 6.95-7.1 (m, 3H), 5.93 (s, 1H), 5.77 (s, 1H), 5.17 (s, 2H). 14-024  (A) δ 7.57 (d, J = 2.7 Hz, 1H), 7.2-7.55 (m, 4H), 6.9-7.15 (m, 3H), 5.96 (s, 1H), 5.78 (s, 1H), 5.19 (s, 2H). 14-025  (A) δ 8.27 (s, 1H), 7.99 (s, 1H), 7.15-7.6 (m, 4H), 6.00 (s, 1H), 5.83 (s, 1H). 14-026  (A) δ 7.74 (s, 1H), 7.69 (d, J = 7.7 Hz, 1H), 7.58 (d, J = 7.7 Hz, 1H), 7.46 (t, J = 7.7 Hz, 1H), 6.04 (s, 1H), 5.82 (s, 1H). 14-027  (A) δ 8.34 (s, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H), 7.60 (t, J = 8.0 Hz, 1H), 6.14 (s, 1H), 5.93 (s, 1H).

Test Examples

Next, usefulness of the compound of the present invention as a pesticide is specifically explained in the following Test Examples to which the present invention is not limited.

Test Example 1 Insecticidal Test Against Cabbage Moth

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-cabbage moth (Plutella xylostella) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the following calculation equation. Incidentally, the test was carried out with two districts.

Rate of dead insects (%)=(Number of dead insects/Number of released insects)×100

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-005, 1-006, 1-015, 1-016, 1-025, 1-031, 1-040, 1-041, 1-053, 1-055˜1-058, 1-062-1-074, 1-076, 1-077, 1-079˜1-096, 1-098, 1-101, 1-102, 1-104˜1-110, 1-113, 1-114, 1-116˜1-140, 1-145˜147, 1-149˜1-157, 1-159˜1-161, 1-166˜1-168, 1-171, 1-172, 1-174, 1-175, 1-176*, 1-177*, 1-178˜1-184, 1-185*, 1-187, 1-188*, 189*, 1-190, 1-194, 1-196, 1-199, 1-206*, 1-207, 1-209, 1-212, 1-214, 1-215, 1-225, 1-226, 2-001˜2-005, 2-011˜2-021, 2-022*, 2-024˜2-027, 2-028**, 2-029**, 2-030, 2-031, 2-032*, 2-033, 2-034**, 2-035**, 2-036˜2-041, 2-042**, 2-043, 2-044**, 2-045**, 2-046**, 2-047*, 2-048**, 2-049**, 2-050*, 2-051*, 2-052, 2-053, 2-054**, 2-055**, 2-057*, 2-058*, 2-059*, 2-060*, 2-061*, 2-062*, 2-063*, 2-064, 2-065*, 2-066, 2-067*, 2-068*, 2-069, 3-002˜3-004, 3-006, 3-007, 3-012, 3-018, 3-023, 3-025˜3-028, 3-030˜3-035, 3-037, 3-038, 3-040, 3-043, 3-044, 3-046, 3-047, 3-050, 3-055, 3-058*, 3-060, 3-061*, 3-062˜3-067, 3-068*, 3-069, 3-070*, 3-071*, 3-073˜3-075, 3-077˜3-081, 3-084, 3-085*, 3-086*, 3-087˜3-089, 3-090*, 3-091*, 3-092*, 3-093*, 3-094˜3-098, 3-100*, 3-102˜3-104, 3-105*, 3-106˜3-108, 3-109*, 3-110*, 3-111*, 3-112*, 3-113*, 3-114, 3-115, 3-116*, 3-117, 3-119˜3-127, 3-129, 3-131, 3-132*, 3-133˜3-136, 3-138˜3-141, 3-143, 3-146, 3-148, 3-150, 3-151**, 4-002, 4-003*, 4-004*, 4-005, 4-006*, 4-008˜4-010, 5-001*, 5-002*, 5-003*, 5-004*, 5-005*, 5-006, 5-007, 5-008*, 5-009*, 5-010*, 5-011*, 5-012*, 5-013*, 5-014*, 5-015*, 5-016, 5-017, 5-019, 5-022*, 5-023*, 5-029*, 5-030˜5-035, 5-036*, 5-037*, 5-038*, 5-039*, 5-040*, 5-041*, 5-042, 5-043, 5-044*, 5-045*, 5-046*, 5-047*, 5-048*, 5-049*, 5-050*, 5-051*, 5-052*, 5-053*, 5-054˜5-056, 5-057*, 5-058*, 5-059*, 5-060*, 5-061*, 5-062*, 5-063*, 5-064*, 5-065*, 5-066, 5-067*, 5-068*, 5-069*, 5-070*, 5-071*, 5-072*, 5-073*, 5-074*, 5-075, 5-075(+)*, 5-075(−), 5-076*, 5-077*, 5-078*, 5-079˜5-082, 5-083*, 5-084, 5-085*, 5-086*, 5-087*, 5-088*, 5-089*, 5-090**, 5-091*, 5-092*, 5-093*, 5-094*, 5-095, 5-097, 5-098, 5-099, 5-100*, 5-101*, 5-102*, 5-103*, 5-104*, 5-105*, 5-106˜5-108, 5-109*, 5-110, 5-111*, 5-112*, 5-113*, 5-114*, 5-115, 5-116, 5-117*, 5-118*, 5-119*, 5-120**, 5-121*, 5-122*, 5-123*, 5-124**, 5-125, 5-126*, 5-127, 5-128*, 5-129, 5-130*, 5-131˜5-133, 5-134*, 5-135˜5-137, 5-138*, 5-139*, 5-140*, 5-141*, 5-142*, 5-143, 5-144*, 5-145*, 5-146, 5-147*, 5-148*, 5-149, 5-150, 5-151*, 5-151(+)*, 5-151(−), 5-152˜5-155, 5-156*, 5-158, 5-159, 5-160*, 5-161**, 5-162*, 5-163, 5-164, 5-165*, 5-166*, 5-167, 5-168**, 5-169*, 5-170˜5-172, 5-173**, 5-174**, 5-175, 5-176*, 5-177, 5-178, 5-179*, 5-180*, 5-181*, 5-182*, 5-183*, 5-184, 5-185*, 5-186*, 5-187*, 5-188*, 5-189**, 5-189(+)*, 5-189(−), 5-190(+)*, 5-190(−), 5-191*, 5-192*, 5-193*, 5-194*, 5-195**, 5-196**, 5-197**, 5-198˜5-200, 5-201*, 5-202*, 5-203**, 5-204, 5-205*, 5-206*, 5-207, 5-208**, 5-209, 5-210*, 5-211*, 5-212*, 5-213*, 5-214*, 5-215*, 5-216*, 5-217**, 5-218*, 5-219*, 5-219(+)*, 5-219(−)*, 5-220*, 5-221, 5-222*, 5-223*, 5-224*, 5-225*, 5-226*, 5-227*, 5-228*, 5-229*, 5-230*, 5-231*, 5-232*, 5-233*, 5-234*, 5-235**, 5-236*, 5-237, 5-238*, 5-239*, 5-240*, 5-241*, 5-242*, 5-243*, 5-244, 5-245*, 5-246*, 5-247*, 5-248, 5-249*, 5-250, 5-251*, 5-252, 5-253, 5-254*, 5-255, 5-256*, 5-257*, 5-258**, 5-259*, 5-260, 5-261*, 5-262**, 5-263**, 5-264*, 5-265*, 5-266, 5-267*, 5-268*, 5-270, 5-271, 5-272*, 5-273*, 5-274*, 5-275*, 5-276*, 5-277*, 5-278*, 5-279*, 5-280, 5-281, 5-282*, 5-283*, 5-284*, 5-285*, 5-286*, 5-287, 5-288*, 5-289*, 5-290, 5-291*, 5-292, 5-293, 5-294*, 5-295*, 5-296, 5-298, 5-299*, 5-300*, 5-301*, 5-302, 5-303*, 5-304, 5-305**, 5-306*, 5-307*, 5-308**, 5-309*, 5-310**, 5-311, 5-312*, 5-313*, 5-314*, 5-315*, 5-316, 5-317*, 5-318*, 5-319*, 5-320*, 5-321, 5-322, 5-323*, 5-324˜5-326, 5-328, 5-329*, 5-330*, 5-331*, 5-332*, 5-333*, 5-334*, 5-335*, 5-336*, 5-337, 5-338*, 5-339*, 5-340, 5-341, 5-342*, 5-343*, 5-344*, 5-345, 5-346*, 5-347, 5-349*, 5-350˜5-352, 5-353*, 5-354*, 5-355*, 5-356*, 5-357*, 5-358*, 5-359**, 5-360*, 5-361*, 5-362*, 5-363, 5-366, 5-372, 5-374*, 5-375*, 5-376**, 5-377**, 5-378*, 5-379**, 5-380**, 5-381*, 5-383*, 5-384*, 5-385**, 5-386**, 5-387*, 5-389*, 5-390*, 5-391, 5-392*, 5-393*, 5-395*, 5-396**, 5-397*, 5-398*, 5-399*, 5-400*, 5-401*, 5-402*, 5-403˜5-407, 5-408*, 5-409, 5-410*, 5-411*, 5-412*, 5-413*, 5-414, 5-415*, 5-416, 5-417*, 5-418*, 5-419*, 5-420*, 5-421*, 5-422*, 5-423*, 5-424*, 5-425*, 5-426*, 5-427*, 5-428*, 5-429*, 5-430*, 5-431, 5-432*, 5-433*, 5-434*, 5-436˜5-438, 5-439*, 5-440*, 5-441*, 5-442*, 5-443*, 5-444*, 5-445*, 5-446*, 5-447˜5-450, 5-452*, 5-453*, 5-454*, 5-455*, 5-456, 5-457, 5-458*, 5-459*, 5-460*, 5-461*, 5-462*, 5-463**, 5-464**, 5-465**, 5-466**, 5-467*, 5-468**, 5-469**, 5-470**, 5-471*, 5-472*, 5-473*, 5-474*, 5-475**, 5-476*, 5-477**, 5-478**, 5-479, 5-480*, 5-481˜5-486, 5-487**, 5-488**, 5-489*, 5-490˜5-493, 5-494**, 5-495**, 5-496**, 5-497**, 5-498**, 5-499**, 5-500*, 5-501˜5-505, 5-507, 5-508, 5-509**, 5-510**, 5-511**, 5-512*, 5-513*, 5-514*, 5-515*, 5-516*, 5-517*, 5-518, 5-519*, 5-520*, 5-521*, 5-522*, 5-523*, 5-524, 5-525, 5-526*, 5-527*, 5-528*, 5-529*, 5-530*, 5-531*, 5-532, 5-533*, 5-534, 5-535, 5-536*, 5-537*, 5-538*, 5-539*, 5-540, 5-540(+)*, 5-541*, 5-541(R), 5-541(S)*, 5-542, 5-543*, 5-544*, 5-545, 5-546*, 5-547*, 5-548*, 5-549*, 5-550, 5-551*, 5-552*, 5-553*, 5-554*, 5-555*, 5-556, 5-557*, 5-558*, 5-559˜5-565, 5-566*, 5-567, 5-568*, 5-569*, 5-570*, 5-571, 5-572*, 5-573*, 5-574*, 5-575*, 5-576*, 5-577*, 5-578*, 5-579*, 5-580*, 5-581*, 5-582*, 5-583*, 5-584*, 5-585*, 5-586*, 5-587*, 5-588*, 5-589*, 5-590*, 5-591, 5-592, 5-593*, 5-594*, 5-595*, 5-596*, 5-597*, 5-598*, 5-599*, 5-600*, 5-601, 5-602, 5-603, 5-604*, 5-605**, 5-606**, 5-607*, 5-608**, 5-609, 5-610, 5-611*, 5-612**, 5-613**8, 5-614*, 5-615*, 5-616*, 5-617*, 5-618, 5-619*, 5-620˜5-622, 5-623*, 5-624*, 5-625*, 5-626, 5-627**, 5-628**, 5-629*, 5-630*, 5-631*, 5-632*, 5-633*, 5-634*, 5-635*, 5-636, 5-637*, 5-638*, 5-639*, 5-640, 5-641*, 5-642**, 5-643*, 5-644**, 5-645*, 5-646*, 5-648*, 5-651, 5-653*, 5-654*, 5-655**, 5-656**, 5-657**, 5-658, 5-659*, 5-660**, 5-661, 5-662**, 5-663, 5-664**, 5-665*, 5-666**, 5-667*, 5-668**, 5-669*, 5-670*, 5-671**, 5-672**, 5-674**, 5-676*, 5-678, 5-684*, 5-685*, 5-686**, 6-001*, 6-002, 6-003*, 6-004**, 6-005, 6-006**, 6-007*, 6-008*, 6-009, 6-010, 6-011*, 6-012, 6-013*, 6-015**, 6-016*, 6-017*, 6-018*, 6-019*, 6-020*, 6-021*, 6-022**, 6-023*, 6-024*, 6-025, 6-026*, 6-027*, 6-028*, 6-029*, 6-030, 6-031*, 6-032*, 6-033*, 6-034*, 6-035*, 6-036*, 6-037*, 6-038*, 6-039*, 6-040*, 6-041*, 6-042*, 6-043*, 6-044*, 6-045*, 6-046*, 6-047*, 6-048*, 6-049*, 6-050*, 6-051*, 6-052, 6-053, 6-054*, 6-055*, 6-056*, 6-057, 6-058*, 6-059*, 6-060**, 6-061, 6-062*, 6-063*, 6-064**, 6-065**, 6-066*, 6-067**, 6-071*, 6-074*, 6-075*, 6-076*, 6-077*, 6-078*, 6-079*, 6-080*, 6-080(+)*, 6-080(−)*, 6-082*, 6-083*, 6-084*, 6-085˜6-088, 6-089, 6-090*, 6-091*, 6-092**, 6-093**, 6-094**, 6-095**, 6-096*, 6-097, 6-099, 6-100**, 6-101**, 6-102**, 6-103**, 6-104*, 6-105, 6-106, 6-108, 6-109, 6-110, 6-111, 6-112, 6-113, 6-114, 6-115*, 6-116, 6-117˜6-120, 6-121*, 6-122, 6-123*, 6-124*, 6-125**, 6-126*, 6-127, 6-129*, 6-130**, 6-131**, 6-132**, 6-133**, 7-001, 7-002*, 7-003*, 7-004*, 7-005*, 7-006*, 7-007*, 7-008*, 7-009*, 7-010*, 8-002*, 8-003*, 8-004, 8-005, 8-006*, 8-007*, 9-003, 9-008˜9-011, 10-001, 10-002*, 10-003˜10-005, 10-006*, 11-006, 11-018, 11-024, 11-025*, 11-026*, 11-038, 11-043, 11-045, 11-046, 11-049*, 11-050-11-052, 11-054, 11-056, 11-058˜11-062, 11-066, 11-075, 11-088, 11-089, 11-098*, 11-099*, 11-101˜11-107, 11-108*, 11-109*, 11-110-11-117, 11-119, 11-120*, 11-122, 11-124*, 11-125*, 11-128, 11-129, 11-132, 12-001, 12-002, 12-008. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm, and the indication “**” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 10 ppm.

Test Example 2 Insecticidal Test Against Common Cutworm

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-common cutworm (Spodoptera litura) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-005, 1-015, 1-016, 1-057, 1-058, 1-062, 1-066, 1-069, 1-080, 1-081, 1-088, 1-101, 1-102, 1-105˜1-109, 1-118, 1-122, 1-123, 1-125, 1-127, 1-129, 1-130, 1-132, 1-153, 1-156, 1-157, 1-166˜1-168, 1-175, 1-176, 1-177*, 1-182˜1-184, 1-185*, 1-188*, 1-189*, 1-194, 1-206*, 1-207, 1-212, 1-214, 1-215, 1-225, 2-002, 2-003, 2-013, 2-019˜2-021, 2-022*, 2-024˜2-026, 2-028, 2-029, 2-031, 2-032, 2-034˜2-039, 2-041, 2-042, 2-044˜2-046, 2-047*, 2-048, 2-049, 2-050*, 2-051*, 2-052*, 2-054˜2-056, 2-057*, 2-058*, 2-059*, 2-061*, 2-062*, 2-064, 2-065*, 2-067*, 2-068*, 3-006, 3-018, 3-026, 3-030, 3-032˜3-035, 3-037, 3-043, 3-044, 3-047, 3-058, 3-060˜3-064, 3-068*, 3-069, 3-070*, 3-071*, 3-072, 3-078, 3-079, 3-081, 3-083˜3-086, 3-089, 3-090*, 3-091*, 3-093*, 3-094, 3-095, 3-098, 3-100*, 3-102, 3-103, 3-105*, 3-106, 3-107, 3-109, 3-110*, 3-111*, 3-112*, 3-113*, 3-114, 3-115, 3-116*, 3-117, 3-121, 3-123˜3-126, 3-129, 3-131, 3-132*, 3-135, 3-136, 3-139, 3-140, 3-145, 3-148, 3-150, 3-151**, 4-003*, 4-004, 4-006*, 4-010, 5-001*, 5-002*, 5-003*, 5-004*, 5-005*, 5-006, 5-007, 5-008*, 5-009*, 5-010, 5-011, 5-012*, 5-013*, 5-014*, 5-015*, 5-016, 5-017, 5-019, 5-022*, 5-023*, 5-029*, 5-032, 5-034, 5-035, 5-036*, 5-037*, 5-038*, 5-039*, 5-040*, 5-041*, 5-042, 5-045*, 5-046*, 5-047*, 5-048*, 5-049*, 5-050*, 5-051*, 5-052*, 5-053*, 5-054, 5-057*, 5-058*, 5-059*, 5-060˜5-064, 5-065*, 5-066˜5-068, 5-069*, 5-070*, 5-071*, 5-072*, 5-073˜5-075, 5-075(+)*, 5-076*, 5-077*, 5-078˜5-081, 5-083*, 5-084, 5-085, 5-086*, 5-087*, 5-088*, 5-089*, 5-090, 5-091*, 5-092*, 5-093*, 5-094*, 5-099˜5-101, 5-102*, 5-103*, 5-104*, 5-105*, 5-106, 5-109, 5-111*, 5-112, 5-113*, 5-114*, 5-115, 5-116, 5-117*, 5-118, 5-119*, 5-120, 5-121*, 5-122˜5-126, 5-128*, 5-130, 5-132˜5-134, 5-136, 5-137, 5-138*, 5-139*, 5-140˜5-147, 5-148*, 5-149, 5-151, 5-151(+)*, 5-152˜5-156, 5-159˜5-169, 5-171˜5-178, 5-179*, 5-180, 5-181, 5-182*, 5-183*, 5-184, 5-185*, 5-186*, 5-187*, 5-188*, 5-189, 5-189(+), 5-191*, 5-192*, 5-193˜5-201, 5-202*, 5-203, 5-204, 5-205*, 5-206*, 5-207˜5-209, 5-210*, 5-211*, 5-212*, 5-213*, 5-214*, 5-215*, 5-216*, 5-217, 5-218*, 5-219*, 5-219(+)*, 5-219(−), 5-220*, 5-221, 5-222*, 5-223*, 5-224*, 5-225, 5-226*, 5-227*, 5-228, 5-229, 5-230*, 5-231, 5-232*, 5-233*, 5-234*, 5-235, 5-236*, 5-237*, 5-239, 5-240*, 5-241*, 5-242*, 5-243˜5-245, 5-246*, 5-247*, 5-249*, 5-250, 5-251, 5-254*, 5-256*, 5-257˜5-259, 5-261*, 5-262, 5-263, 5-264*, 5-265*, 5-267, 5-268*, 5-269, 5-271, 5-272*, 5-273*, 5-274*, 5-275˜5-277, 5-278*, 5-279*, 5-280, 5-282*, 5-283*, 5-284, 5-285*, 5-286*, 5-288*, 5-289*, 5-291*, 5-292, 5-294*, 5-295*, 5-296, 5-298, 5-299*, 5-300, 5-301*, 5-302, 5-303, 5-305, 5-306*, 5-307*, 5-308˜5-311, 5-312*, 5-313*, 5-314*, 5-315*, 5-316, 5-317*, 5-318*, 5-319*, 5-320˜5-322, 5-323*, 5-329*, 5-330*, 5-331*, 5-332, 5-333*, 5-334*, 5-335˜5-337, 5-338*, 5-339*, 5-341, 5-342, 5-343*, 5-344*, 5-345, 5-346, 5-349*, 5-351, 5-353, 5-354, 5-355*, 5-356˜5-359, 5-360*, 5-361*, 5-362*, 5-363, 5-374*, 5-375*, 5-376, 5-377, 5-378*, 5-379˜5-386, 5-387*, 5-389*, 5-390*, 5-392*, 5-393*, 5-395, 5-396, 5-397*, 5-398*, 5-399*, 5-400*, 5-401*, 5-402*, 5-405˜5-407, 5-408*, 5-409, 5-410*, 5-411*, 5-412*, 5-413*, 5-415*, 5-417*, 5-418*, 5-419*, 5-420*, 5-421*, 5-422*, 5-423*, 5-424*, 5-425*, 5-426*, 5-427*, 5-428*, 5-429*, 5-430*, 5-432*, 5-433*, 5-434*, 5-437, 5-438, 5-439*, 5-440*, 5-441*, 5-442*, 5-443*, 5-444*, 5-446*, 5-447, 5-452*, 5-453*, 5-454*, 5-455*, 5-458*, 5-459*, 5-460*, 5-461*, 5-462*, 5-463**, 5-464**, 5-465**, 5-466**, 5-467*, 5-468**, 5-469**, 5-470**, 5-471*, 5-472*, 5-473*, 5-474*, 5-475**, 5-476*, 5-477**, 5-478**, 5-479, 5-480*, 5-481˜5-486, 5-487**, 5-488**, 5-489*, 5-490˜5-493, 5-494**, 5-495**, 5-496**, 5-497**, 5-498**, 5-499**, 5-500*, 5-501, 5-503, 5-505, 5-507, 5-508, 5-509**, 5-511**, 5-513*, 5-514*, 5-515*, 5-516*, 5-517*, 5-518, 5-519*, 5-520*, 5-521, 5-522*, 5-523*, 5-526*, 5-527*, 5-528*, 5-529*, 5-530*, 5-531*, 5-532, 5-533*, 5-535, 5-536*, 5-537*, 5-538*, 5-539*, 5-540(+), 5-541*, 5-541(R), 5-541(S)*, 5-542, 5-543*, 5-545, 5-546, 5-548*, 5-549*, 5-551*, 5-552*, 5-553*, 5-554*, 5-555*, 5-556, 5-557*, 5-558*, 5-559, 5-560, 5-562, 5-565, 5-566*, 5-568*, 5-569*, 5-570*, 5-571, 5-572*, 5-573*, 5-574*, 5-575*, 5-576*, 5-577*, 5-578*, 5-579*, 5-580*, 5-581*, 5-582*, 5-583*, 5-584*, 5-585*, 5-586*, 5-587*, 5-588*, 5-589*, 5-590*, 5-592, 5-593*, 5-594*, 5-595*, 5-596*, 5-598*, 5-599*, 5-600*, 5-601*, 5-602, 5-603, 5-604*, 5-605**, 5-606**, 5-607*, 5-608**, 5-609, 5-610, 5-611*, 5-612**, 5-613**, 5-614*, 5-615*, 5-616*, 5-617*, 5-618, 5-619*, 5-621, 5-623*, 5-624*, 5-625*, 5-626, 5-627**, 5-628**, 5-629*, 5-630*, 5-631*, 5-632*, 5-633*, 5-634*, 5-635*, 5-636, 5-637*, 5-638*, 5-639*, 5-641*, 5-642**, 5-643*, 5-644**, 5-645*, 5-646, 5-647, 5-648*, 5-650, 5-651, 5-653*, 5-654*, 5-655**, 5-656**, 5-657**, 5-659*, 5-660**, 5-661*, 5-662**, 5-664**, 5-665*, 5-666**, 5-667*, 5-668*, 5-669*, 5-670*, 5-671**, 5-672**, 5-674**, 5-676**, 5-678, 5-684**, 5-685**, 5-686**, 6-001*, 6-002, 6-003*, 6-004˜6-006, 6-007*, 6-008*, 6-010, 6-012, 6-013, 6-015, 6-016, 6-017*, 6-018, 6-019*, 6-020*, 6-021*, 6-022˜6-025, 6-026*, 6-027*, 6-028˜6-030, 6-031*, 6-032*, 6-033*, 6-034*, 6-035*, 6-036˜6-038, 6-039*, 6-040, 6-041, 6-042*, 6-043*, 6-044, 6-045, 6-046*, 6-047*, 6-048*, 6-049*, 6-050*, 6-051*, 6-053, 6-054*, 6-055*, 6-056, 6-058˜6-067, 6-071, 6-074*, 6-075*, 6-076*, 6-077*, 6-078*, 6-079*, 6-080*, 6-080(+)*, 6-080(−)*, 6-082*, 6-083*, 6-084*, 6-086, 6-087, 6-089*, 6-090*, 6-091*, 6-092**, 6-093**, 6-094**, 6-095**, 6-096*, 6-098*, 6-099, 6-100**, 6-101**, 6-102**, 6-103**, 6-104*, 6-105, 6-106*, 6-110*, 6-111*, 6-112*, 6-114*, 6-120, 6-121*, 6-123*, 6-124*, 6-125**, 6-126*, 6-129*, 6-130**, 6-131**, 6-132**, 6-133**, 7-001, 7-002*, 7-003*, 7-004*, 7-005*, 7-006*, 7-007*, 7-008*, 7-009*, 7-010*, 8-002*, 8-003*, 8-004, 8-005, 8-006*, 8-007*, 9-009, 10-001˜10-005, 10-006*, 11-024, 11-025*, 11-026*, 11-038, 11-049*, 11-052, 11-055, 11-056, 11-061, 11-062, 11-066, 11-070, 11-098*, 11-099*, 11-108*, 11-109*, 11-119, 11-120*, 1-124*, 1125*, 1129, 12-001, 12-002, 12-008. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 3 Insecticidal Test Against Beet Armyworm

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-beet armyworm (Spodoptera exigua) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-015, 1-016, 1-057, 1-058, 1-062˜1-064, 1-066, 1-080, 1-081, 1-088, 1-102, 1-105, 1-106, 1-109, 1-118, 1-122, 1-123, 1-125, 1-127, 1-151, 1-153, 1-155˜1-157, 1-166, 1-175, 1-189, 1-207, 1-214, 1-215, 2-003, 2-019, 2-020, 3-026, 3-027, 3-030, 3-032, 3-037, 3-060, 3-091, 3-093, 3-095, 3-109, 3-110, 3-112, 3-125, 5-001˜5-005, 5-008, 5-009, 5-029, 5-036, 5-037, 5-040, 5-041, 5-045, 5-046, 5-048, 5-049, 5-050, 5-052, 5-053, 5-057˜5-059, 5-061˜5-065, 5-067˜5-069, 5-071, 5-073˜5-075, 5-075(+), 5-076, 5-083, 5-086˜5-089, 5-091, 5-092, 5-094, 5-111, 5-113, 5-117˜5-119, 5-122, 5-138˜5-142, 5-147, 5-148, 5-151, 5-160, 5-165, 5-174, 5-182, 5-183, 5-185˜5-188, 5-189(+), 5-202, 5-205, 5-210˜5-212, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-220, 5-223, 5-226, 5-227, 5-230, 5-232˜5-234, 5-236, 5-239, 5-241, 5-247, 5-251, 5-257, 5-261, 5-264, 5-268, 5-273˜5-275, 5-279, 5-282, 5-283, 5-285, 5-286, 5-288, 5-291, 5-294, 5-295, 5-301, 5-306, 5-307, 5-309, 5-310, 5-312˜5-315, 5-320, 5-321, 5-323, 5-331˜5-334, 5-339, 5-341, 5-355˜5-357, 5-360˜5-362, 5-374, 5-375, 5-378, 5-387, 5-389, 5-390, 5-397, 5-398, 5-412, 5-429, 5-433, 5-440, 5-474, 5-476, 5-478, 5-480, 5-488, 5-494, 5-495, 5-588, 5-604, 5-638, 5-642, 6-017˜6-021, 6-026, 6-027, 6-031, 6-033˜6-041, 6-043˜6-045, 6-048, 6-049, 6-058, 6-059, 6-063˜6-066, 6-074˜6-076, 6-095, 6-131, 7-002, 7-003, 7-005˜7-009, 8-002, 11-024, 11-025, 11-026.

Test Example 4 Insecticidal Test Against Oriental Tea Tortix

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-oriental tea tortix (Homona magnanima) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-015, 1-016, 1-057, 1-058, 1-062, 1-080, 1-105, 1-107, 1-0122, 1-123, 1-125, 1-127, 1-153, 1-156, 1-189, 1-207, 1-214, 1-215, 2-003, 2-034, 2-035, 2-051, 2-052, 3-037, 3-060, 3-095, 3-110, 3-112, 3-125, 3-129, 4-003, 5-001, 5-003˜5-005, 5-008, 5-009, 5-012, 5-013, 5-022, 5-029, 5-037, 5-040, 5-041, 5-045˜5-050, 5-052, 5-053, 5-057˜5-059, 5-061˜5-065, 5-069˜5-071, 5-073, 5-075, 5-075(+), 5-076, 5-077, 5-083, 5-086˜5-090, 5-092˜5-094, 5-102, 5-103, 5-111, 5-113, 5-114, 5-117, 5-119, 5-121, 5-122, 5-138˜5-142, 5-147, 5-148, 5-151, 5-151(+), 5-156, 5-160, 5-161, 5-165, 5-166, 5-180, 5-182, 5-183, 5-185, 5-187, 5-188, 5-189(+), 5-202, 5-205, 5-208, 5-210˜5-212, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-220, 5-221, 5-223, 5-226˜5-228, 5-230, 5-232˜5-234, 5-236, 5-240˜5-242, 5-246, 5-247, 5-251, 5-254, 5-273˜5-275, 5-279, 5-282, 5-283, 5-285, 5-286, 5-288, 5-289, 5-291, 5-294, 5-295, 5-301, 5-306, 5-307, 5-310, 5-312, 5-313, 5-315, 5-319, 5-321, 5-323, 5-329, 5-330, 5-338, 5-339, 5-341, 5-356, 5-357, 5-359, 5-360, 5-362, 5-374, 5-375, 5-378, 5-379, 5-381, 5-387˜5-390, 5-392, 5-393, 5-395˜5-399, 5-401, 5-412, 5-418, 5-419, 5-426, 5-429, 5-430, 5-433, 5-434, 5-441, 5-458˜5-461, 5-463˜5-465, 5-468, 5-470, 5-472, 5-474, 5-476˜5-478, 5-480, 5-488, 5-494, 5-515, 5-519, 5-523, 5-539, 5-541, 5-541(S), 5-553, 5-554, 5-576, 5-579, 5-585, 5-588, 5-594, 5-601, 5-604, 5-606, 5-612, 5-617, 5-638, 5-642, 5-655, 5-656, 6-001, 6-003, 6-017, 6-018, 6-020, 6-021, 6-027, 6-031, 6-033˜6-035, 6-038˜6-041, 6-043, 6-066, 6-075, 6-076, 6-081, 6-093, 6-095, 6-124, 6-131, 7-002˜7-009, 8-002, 11-024, 11-026.

Test Example 5 Insecticidal Test Against Corn Earworm

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 1-corn earworm (Helicoverpa armigera) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with twelve districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-066, 1-153, 1-156, 1-207, 1-214, 1-215, 2-034, 2-035, 2-042, 2-055, 2-057, 2-059, 2-062, 2-063, 2-067, 2-068, 3-027, 3-030, 3-032, 3-086, 3-095, 3-109, 3-110, 3-112, 3-151, 5-008, 5-009, 5-022, 5-040, 5-046, 5-047, 5-049, 5-050, 5-052, 5-053, 5-057˜5-059, 5-061˜5-063, 5-065, 5-068, 5-070, 5-071, 5-075, 5-075(+), 5-076, 5-077, 5-083, 5-086˜5-089, 5-099˜5-101, 5-109, 5-113, 5-117, 5-120˜5-122, 5-126, 5-138, 5-139, 5-141, 5-142, 5-147, 5-148, 5-151, 5-151(+), 5-156, 5-160, 5-165, 5-169, 5-177, 5-180, 5-185, 5-189(+), 5-193, 5-208, 5-210˜5-212, 5-214˜5-219, 5-219(+), 5-223, 5-227, 5-228, 5-230, 5-231, 5-233, 5-234, 5-236, 5-241, 5-245, 5-246, 5-249, 5-251, 5-254, 5-261, 5-264, 5-269, 5-273˜5-275, 5-279, 5-284, 5-286, 5-291, 5-294, 5-295, 5-306, 5-307, 5-309, 5-310, 5-312˜5-315, 5-319, 5-323, 5-331˜5-336, 5-338, 5-339, 5-341, 5-353˜5-355, 5-357, 5-359, 5-360, 5-374, 5-375, 5-378˜5-381, 5-383, 5-384, 5-387, 5-389, 5-390, 5-393, 5-395, 5-397˜5-400, 5-408˜5-413, 5-415, 5-420˜5-424, 5-426, 5-427, 5-429, 5-433, 5-434, 5-440, 5-443, 5-446, 5-452˜5-454, 5-458˜5-470, 5-473˜5-481, 5-483, 5-484, 5-487˜5-489, 5-494˜5-499, 5-508˜5-511, 5-513, 5-515˜5-517, 5-519, 5-522, 5-523, 5-526˜5-529, 5-531˜5-533, 5-538, 5-539, 5-541, 5-541(S), 5-543, 5-548, 5-549, 5-558˜5-560, 5-566, 5-568, 5-570, 5-572˜5-577, 5-579˜5-589, 5-595, 5-599˜5-601, 5-604, 5-606˜5-608, 5-611, 5-612, 5-614˜5-619, 5-623˜5-625, 5-627˜5-639, 5-641˜5-646, 5-654˜5-657, 5-660˜5-662, 5-664˜5-668, 5-671, 5-672, 5-674, 5-676, 5-684, 5-685, 6-003, 6-004, 6-016˜6-019, 6-021, 6-023, 6-024, 6-026, 6-027, 6-031, 6-033˜6-041, 6-043˜6-045, 6-048, 6-049, 6-056, 6-066, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-084, 6-091˜6-095, 6-098, 6-100, 6-102˜6-106, 6-110, 6-111, 6-124, 6-126, 6-130˜6-132, 7-002˜7-009, 8-002, 8-005˜8-007, 10-006, 11-024, 11-125, 11-130.

Test Example 6 Insecticidal Test Against Peach Fruit Moth

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped apple young fruits on which peach fruit moth (Carpocina sasakii) laid eggs (20-egg/fruit) for about 10 seconds, and after air-drying, they were placed in a laboratory dish, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 20 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 5-049, 5-050, 5-070, 5-076, 5-083, 5-088, 5-111, 5-148, 5-219, 5-219(+), 5-221, 5-234, 5-286, 5-291, 5-323, 5-360, 5-387, 5-390, 5-398, 5-480, 5-494, 6-027, 6-039, 7-008.

Test Example 7 Insecticidal Test Against Frankliniella occidentalis

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid theron, and 10-Frankliniella occidentalis with first instar larva per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-175, 1-177˜1-179, 1-182, 2-020, 2-022, 2-028*, 2-029*, 2-032, 2-033, 2-034*, 2-035*, 2-037*, 2-038*, 2-039*, 2-040*, 2-041*, 2-042*, 2-043*, 2-044*, 2-045*, 2-046*, 2-047, 2-048*, 2-049*, 2-050˜2-052, 2-057˜2-068, 3-068, 3-072*, 3-080, 3-084˜3-086, 3-090, 3-093, 3-105, 3-107, 3-109, 3-110, 3-1,2,3-114, 3-122˜3-125, 3-132, 3-135, 3-136, 3-151, 4-004, 4-006, 5-001, 5-003, 5-009, 5-013, 5-022, 5-023, 5-029, 5-037˜5-041, 5-044˜5-053, 5-057˜5-075, 5-075(+), 5-076˜5-078, 5-081˜5-089, 5-090*, 5-091˜5-094, 5-099˜5-105, 5-109, 5-111˜5-119, 5-120*, 5-121˜5-123, 5-124*, 5-126˜5-128, 5-129*, 5-130, 5-131*, 5-134, 5-137˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158˜5-160, 5-161*, 5-162, 5-164˜5-166, 5-167*, 5-168*, 5-169, 5-171, 5-172*, 5-178˜5-188, 5-189(+), 5-190(+), 5-191˜5-194, 5-201, 5-202, 5-205˜5-207, 5-208*, 5-210˜5-216, 5-217*, 5-218, 5-219, 5-219(+), 5-219(−), 5-220˜5-234, 5-236˜5-242, 5-244˜5-247, 5-249, 5-251˜5-254, 5-255*, 5-256, 5-257, 5-258*, 5-259˜5-261, 5-264, 5-265, 5-269*, 5-270, 5-271*, 5-272˜5-283, 5-284˜5-289, 5-291, 5-292, 5-294, 5-295, 5-297, 5-299, 5-300, 5-301, 5-302*, 5-303, 5-306, 5-307, 5-309, 5-310*, 5-311˜5-315, 5-318, 5-319, 5-321˜5-323, 5-329˜5-336, 5-338, 5-339, 5-341˜5-346, 5-348, 5-349, 5-353˜5-358, 5-360˜5-362, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387˜5-393, 5-395, 5-396*, 5-397˜5-401, 5-403˜5-406, 5-408˜5-413, 5-415, 5-417˜5-430, 5-432˜5-434, 5-439˜5-443, 5-445, 5-446, 5-449, 5-452, 5-453, 5-455, 5-458˜5-503, 5-507˜5-512, 5-514˜5-516, 5-518, 5-519, 5-521˜5-525, 5-527˜5-534, 5-537˜5-539, 5-541, 5-541(S), 5-542, 5-543, 5-545˜5-549, 5-550˜5-562, 5-564, 5-565, 5-567˜5-576, 5-579˜5-590, 5-592, 5-599˜5-601, 5-604˜5-609, 5-611, 5-612, 5-614˜5-619, 5-621, 5-623, 5-624, 5-626˜5-639, 5-641˜5-648, 5-650, 5-651, 5-653˜5-672, 5-674, 5-676, 5-678, 5-684˜5-686, 6-001˜6-003, 6-004*, 6-005*, 6-006*, 6-007˜6-013, 6-015*, 6-016˜6-021, 6-022*, 6-023, 6-024*, 6-025*, 6-026˜6-050, 6-054˜6-056, 6-058, 6-059, 6-063, 6-066, 6-070, 6-071*, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-086, 6-089˜6-111, 6-113˜6-115, 6-117, 6-119˜6-124, 6-126, 6-127, 6-129˜6-133, 7-001, 7-003˜7-010, 8-002, 8-003, 8-005, 8-006, 10-002, 10-005, 10-006, 11-024˜11-026, 11-043, 11-045, 11-054˜11-056, 11-059, 11-070, 11-089, 11-099, 11-107, 11-114, 11-120, 11-125, 11-128˜11-130, 11-132, 12-002, 12-007, 12-008. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 8 Insecticidal Test Against Thrips palmi

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10-Thrips palmi in the stage of adult per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-179, 1-196, 2-022, 2-024˜2-026, 2-028, 2-029, 2-033, 2-035, 2-039, 2-044˜2-048, 2-050˜2-052, 2-057˜2-059, 2-061, 2-063, 2-065, 2-067, 3-079, 3-085, 3-086, 3-091, 3-110, 3-112, 3-124, 3-131, 3-148, 3-151, 4-003˜4-005, 4-010, 5-001, 5-003, 5-006, 5-008, 5-012˜5-015, 5-022, 5-023, 5-029, 5-036, 5-037, 5-040, 5-045˜5-053, 5-057˜5-063, 5-065, 5-067, 5-068, 5-070˜5-075, 5-075(+), 5-076˜5-079, 5-081˜5-084, 5-086˜5-093, 5-099, 5-102˜5-104, 5-111˜5-114, 5-117˜5-121, 5-124, 5-128˜5-130, 5-137˜5-148, 5-151, 5-151(+), 5-153, 5-156, 5-160˜5-162, 5-165, 5-166, 5-179, 5-180, 5-182˜5-186, 5-188, 5-189(+), 5-193, 5-202, 5-205, 5-206, 5-208˜5-210, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-220, 5-224˜5-226, 5-228˜5-230, 5-232˜5-234, 5-236, 5-238, 5-239, 5-242, 5-246, 5-247, 5-251, 5-256˜5-258, 5-261, 5-264, 5-269, 5-273˜5-276, 5-278, 5-279, 5-280, 5-282, 5-283, 5-285, 5-286, 5-288, 5-289, 5-291, 5-294, 5-295, 5-299, 5-303, 5-306, 5-309, 5-310, 5-312˜5-314, 5-319, 5-322, 5-323, 5-329, 5-330, 5-332, 5-334, 5-335, 5-338, 5-339, 5-346, 5-349, 5-353˜5-362, 5-374, 5-375, 5-378˜5-381, 5-383˜5-385, 5-387, 5-389, 5-390, 5-395˜5-401, 5-408˜5-413, 5-415, 5-418˜5-424, 5-426, 5-427, 5-429, 5-430, 5-432˜5-434, 5-439˜5-443, 5-446, 5-452˜5-455, 5-458˜5-470, 5-471˜5-492, 5-494˜5-501, 5-508˜5-513, 5-515, 5-516, 5-519, 5-521˜5-523, 5-525, 5-527˜5-531, 5-533, 5-536, 5-538, 5-539, 5-541, 5-541(S), 5-543, 5-547, 5-549, 5-553˜5-555, 5-560, 5-564, 5-568˜5-570, 5-572˜5-576, 5-579, 5-581, 5-582, 5-584˜5-590, 5-593, 5-598˜5-601, 5-604˜5-609, 5-611˜5-613, 5-616˜5-619, 5-621, 5-623˜5-625, 5˜627˜5-639, 5-641˜5-648, 5-650, 5-651, 5-655˜5-657, 5-659˜5-662, 5-664˜5-669, 5-672, 5-674, 5-676, 5-684, 5-685, 6-001, 6-003˜6-008, 6-015, 6-017˜6-024, 6-026˜6-035, 6-037˜6-041, 6-043˜6-045, 6-047˜6-049, 6-054˜6-056, 6-058, 6-059, 6-063, 6-066, 6-070, 6-073˜6-080, 6-080(+), 6-080(−), 6-081˜6-084, 6-089, 6-090, 6-092˜6-096, 6-098˜6-107, 6-109˜6-111, 6-114, 6-115, 6-120, 6-121, 6-123, 6-124, 6-130˜6-133, 7-003, 7-005˜7-009, 8-002, 8-006, 8-007, 9-011, 10-002, 10-006, 11-025, 11-026, 11-054, 11-056, 11-059, 11-125, 11-129, 12-002, 12-008.

Test Example 9 Insecticidal Test Against Eysarcoris lewisi

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leave sheaths of rice for about 10 seconds, and after air-drying, they were placed in a test tube, then 5-Eysarcoris lewisi in the stage of first instar larva per the test tube were released therein, and the test tube was covered with a sponge and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-015, 1-050, 1-051, 1-175, 1-209, 2-029, 2-034, 2-035, 2-042, 2-044˜2-052, 2-054, 2-055, 2-057˜2-059, 2-061, 2-062, 2-065, 2-067, 2-068, 3-047, 3-068, 3-070˜3-072, 3-086, 3-090, 3-093, 3-106, 3-109˜3-112, 3-114, 3-125, 3-131, 3-151, 5-001, 5-003, 5-005, 5-008, 5-009, 5-013˜5-015, 5-017, 5-022, 5-023, 5-026, 5-029, 5-037˜5-041, 5-045˜5-053, 5-058˜5-065, 5-067˜5-069, 5-071˜5-075, 5-075(+), 5-076˜5-078, 5-081, 5-083, 5-084˜5-094, 5-099˜5-105, 5-111˜5-114, 5-116˜5-122, 5-124, 5-126, 5-128, 5-130, 5-134, 5-137˜5-142, 5-144, 5-145, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-154, 5-156, 5-158˜5-162, 5-165, 5-166, 5-168, 5-169, 5-171, 5-173, 5-174, 5-179˜5-189, 5-189(+), 5-191, 5-195˜5-197, 5-203, 5-205, 5-206, 5-208˜5-210, 5-212˜5-216, 5-218, 5-219, 5-219(+), 5-220˜5-230, 5-232, 5-233, 5-235, 5-236, 5-238˜5-247, 5-249, 5-251, 5-254, 5-256˜5-262, 5-264, 5-265, 5-273˜5-279, 5-283, 5-285, 5-286, 5-288, 5-289, 5-291, 5-294, 5-295, 5-299˜5-301, 5-304˜5-310, 5-312˜5-315, 5-318˜5-321, 5-323, 5-329, 5-330, 5-332, 5-334, 5-335, 5-338, 5-339, 5-341˜5-344, 5-346, 5-348, 5-353˜5-360, 5-362, 5-374˜5-387, 5-389, 5-390, 5-392, 5-393, 5-395˜5-401, 5-403˜5-405, 5-408˜5-413, 5-415, 5-417˜5-424, 5-426˜5-429, 5-431˜5-434, 5-440, 5-443, 5-445, 5-446, 5-448, 5-452˜5-455, 5-457˜5-465, 5-467˜5-470, 5-472˜5-478, 5-480, 5-487˜5-489, 5-491, 5-492, 5-494˜5-500, 5-505, 5-509, 5-510, 5-512, 5-515˜5-517, 5-519˜5-523, 5-526˜5-533, 5-537˜5-539, 5-541, 5-541(S), 5-543, 5-546, 5-547, 5-549, 5-551˜5-558, 5-562, 5-568˜5-570, 5-572˜5-577, 5-579, 5-582˜5-588, 5-593, 5-595, 5-598, 5-600, 5-601, 5-604, 5-606, 5-611, 5-612, 5-614˜5-617, 5-619, 5-621, 5-623, 5-627, 5-631, 5-635˜5-638, 5-642, 5-643, 5-646, 5-648, 5-654˜5-657, 5-660, 5-661, 5-664, 5-668, 5-670, 5-672, 5-674, 5-684˜5-686, 6-001, 6-006˜6-013, 6-015˜6-024, 6-026˜6-029, 6-031˜6-051, 6-054˜6-056, 6-058˜6-060, 6-062˜6-067, 6-070, 6-071, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-086, 6-089˜6-093, 6-095, 6-098˜6-103, 6-110˜6-112, 6-114˜6-118, 6-121, 6-124, 6-129˜6-132, 7-002˜7-010, 10-006, 11-060, 11-098, 11-125.

Test Example 10 Insecticidal Test Against Brown Rice Planthopper

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leave sheaths of rice for about 10 seconds, and after air-drying, they were placed in a test tube, then 5-brown rice planthopper (Nilaparvata lugens) in the second instar larva per the test tube were released therein, and the test tube was covered with a sponge and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-005˜1-007, 1-017, 1-061, 1-154, 1-175, 1-185, 1-188, 1-189, 2-018, 2-020, 2-025˜2-027, 2-029, 2-033, 2-034, 2-036, 2-044, 2-046, 2-051, 2-052, 2-054, 2-057˜2-059, 2-062, 2-065, 2-068, 3-013, 3-068, 3-070, 3-072, 3-075, 3-109, 3-112, 3-125, 3-151, 5-001, 5-003, 5-009, 5-013, 5-015, 5-023, 5-029, 5-040, 5-041, 5-049, 5-050, 5-053, 5-058, 5-060, 5-061, 5-063, 5-065˜5-068, 5-070˜5-074, 5-075(+), 5-076, 5-077, 5-080, 5-081, 5-083, 5-084, 5-086˜5-088, 5-090˜5-094, 5-099, 5-102, 5-106, 5-111, 5-113, 5-117˜5-120, 5-130, 5-138˜5-148, 5-151, 5-151(+), 5-152˜5-156, 5-160, 5-161, 5-163, 5-170, 5-173, 5-174, 5-182, 5-186, 5-189, 5-189(+), 5-195, 5-197, 5-203, 5-205, 5-208, 5-210, 5-212, 5-214, 5-216, 5-219, 5-219(+), 5-220, 5-226, 5-230˜5-232, 5-234˜5-236, 5-239, 5-240, 5-242, 5-243, 5-245, 5-246, 5-251, 5-254, 5-257, 5-258, 5-261, 5-262, 5-264, 5-265, 5-273˜5-275, 5-279, 5-280, 5-285, 5-286, 5-288, 5-294, 5-295, 5-305˜5-310, 5-313, 5-315, 5-323, 5-330, 5-335, 5-339, 5-341, 5-344, 5-353˜5-360, 5-374˜5-377, 5-379˜5-388, 5-390, 5-392, 5-393, 5-396, 5-398˜5-401, 5-405, 5-410, 5-412, 5-413, 5-419, 5-421˜5-423, 5-426, 5-427, 5-429, 5-432, 5-433, 5-440, 5-453, 5-455, 5-460, 5-461, 5-463˜5-465, 5-467, 5-470, 5-472˜5-476, 5-482, 5-483, 5-487, 5-490˜5-492, 5-494˜5-496, 5-498, 5-499, 5-501, 5-510˜5-512, 5-515, 5-519, 5-521, 5-523, 5-525, 5-527˜5-530, 5-532, 5-537˜5-539, 5-541, 5-541(S), 5-546, 5-547, 5-550˜5-554, 5-560, 5-568, 5-570, 5-572˜5-576, 5-579, 5-583, 5-585, 5-586, 5-588, 5-608, 5-614, 5-617, 5-619, 5-621, 5-627, 5-628, 5-636, 5-637, 5-642, 5-646, 5-648, 5-651, 5-654, 5-656, 5-657, 5-660, 5-662, 5-664, 5-670, 5-672, 5-674, 5-684, 5-686, 6-001, 6-003, 6-007, 6-015˜6-023, 6-027˜6-045, 6-048˜6-050, 6-056, 6-058˜6-065, 6-076˜6-080, 6-080(+), 6-080(−), 6-081˜6-083, 6-086, 6-090˜6-093, 6-096, 6-098, 6-100˜6-103, 6-105, 6-114, 6-115, 6-117, 6-124, 6-125, 6-130˜6-132, 7-001˜7-004, 7-006, 7-008, 7-009, 8-003, 9-009, 11-039, 11-041, 11-054, 11-098, 11-101, 11-132.

Test Example 11 Insecticidal Test Against Bemisia argentifolii

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a tomato cut out on which Bemisia argentifolii laid eggs (10-egg/leaf) was laid thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-011, 1-182, 2-024*, 2-025*, 2-026*, 2-028*, 2-029*, 2-033, 2-034*, 2-035*, 2-037*, 2-044*, 2-047, 2-050, 2-051, 2-058˜2-062, 2-065, 2-066, 3-068, 3-079, 3-090, 3-112, 3-125, 3-151, 4-003, 4-006, 5-001, 5-003, 5-005, 5-007, 5-009, 5-011, 5-013˜5-015, 5-021˜5-023, 5-029, 5-035, 5-037˜5-041, 5-045˜5-053, 5-057˜5-061, 5-063, 5-065, 5-067˜5-075, 5-075(+), 5-076˜5-078, 5-079*, 5-081, 5-084˜5-089, 5-090*, 5-091˜5-094, 5-099˜5-104, 5-112˜5-114, 5-117, 5-118, 5-120*, 5-122, 5-123, 5-126, 5-128, 5-130, 5-137˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-148, 5-151, 5-151(+), 5-153, 5-154, 5-156, 5-158˜5-160, 5-161*, 5-162, 5-164, 5-165, 5-167*, 5-171, 5-180, 5-182˜5-188, 5-189(+), 5-191, 5-193, 5-201, 5-202, 5-205˜5-207, 5-208*, 5-209˜5-216, 5-218, 5-219, 5-219(+), 5-220˜5-223, 5-225˜5-234, 5-236, 5-238˜5-242, 5-245˜5-247, 5-249, 5-254, 5-258*, 5-261, 5-264, 5-273˜5-275, 5-277˜5-279, 5-281, 5-285˜5-288, 5-291, 5-292, 5-294, 5-295, 5-297, 5-299, 5-301, 5-306, 5-309, 5-310*, 5-312˜5-315, 5-318, 5-319, 5-321, 5-323, 5-330, 5-332, 5-335, 5-339, 5-341, 5-344, 5-345, 5-353-5-358, 5-359*, 5-360, 5-362, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387˜5-393, 5-396*, 5-397˜5-401, 5-405, 5-409, 5-410, 5-412, 5-417, 5-418, 5-421˜5-423, 5-426˜5-428, 5-430, 5-433, 5-434, 5-440, 5-446, 5-453, 5-455, 5-458, 5-460, 5-461, 5-463˜5-465, 5-468˜5-488, 5-490˜5-498, 5-509, 5-510, 5-515, 5-516, 5-519, 5-521˜5-523, 5-525, 5-527˜5-532, 5-538, 5-539, 5-541, 5-543, 5-549, 5-551˜5-555, 5-557, 5-558, 5-560, 5-562, 5-569˜5-576, 5-579, 5-583˜5-589, 5-600, 5-604˜5-607, 5-611, 5-612, 5-616˜5-619, 5-623, 5-628, 5-630, 5-631, 5-637˜5-639, 5-642, 5-646˜5-648, 5-650˜5-657, 5-660˜5-662, 5-664, 5-665, 5-667, 5-668, 5-671, 5-672, 5-674, 5-684˜5-686, 6-001, 6-003, 6-009, 6-011˜6-013, 6-016˜6-018, 6-020, 6-021, 6-022*, 6-027, 6-028, 6-031˜6-041, 6-043, 6-044, 6-048˜6-050, 6-056, 6-074˜6-076, 6-078, 6-079, 6-081, 6-083, 6-089, 6-090, 6-093, 6-095, 6-096, 6-098, 6-100, 6-102, 6-110, 6-114, 6-124, 6-130˜6-132, 7-001, 7-003˜7-006, 7-008˜7-010, 11-017, 11-024, 11-026, 11-028, 11-056, 11-099, 11-120, 11-125, 11-132. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 12 Insecticidal Test Against Green Peach Aphid

A wet cotton wool was laid in a laboratory dish having an inner diameter of 3 cm, a leaf of a cabbage cut out so as to have the same diameter was laid theron, and 4-green peach aphid (Myzus persicae) in the stage of no-wing adult was left. After 1 day, a 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm, and the chemical solution was sprayed with a rotating spray tower (2.5 mg/cm²), and the laboratory dish was covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-006, 1-063, 1-067, 1-069, 1-153, 1-158, 1-163, 1-166, 1-167, 1-171, 1-175, 1-207, 1-209, 1-215, 2-005, 2-015, 2-017, 2-024*, 2-025*, 2-026*, 2-027, 2-029*, 2-034*, 2-044*, 2-046*, 2-050, 2-051, 2-057˜2-059, 2-062, 2-065, 2-066, 3-006, 3-029, 3-064, 3-068, 3-089, 3-110, 3-114, 3-125, 3-131, 3-139, 3-143, 4-003, 5-001, 5-003, 5-005, 5-009, 5-013, 5-015, 5-022, 5-023, 5-037˜5-041, 5-045˜5-050, 5-052, 5-053, 5-056, 5-058˜5-061, 5-063, 5-065˜5-068, 5-070˜5-075, 5-075(+), 5-076, 5-077, 5-079*, 5-081, 5-083˜5-086, 5-090*, 5-091˜5-094, 5-099, 5-100, 5-102, 5-103, 5-113, 5-117, 5-118, 5-128, 5-130, 5-134, 5-138˜5-142, 5-143, 5-144, 5-145, 5-146, 5-147, 5-148, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158, 5-160, 5-161*, 5-162, 5-165, 5-180˜5-187, 5-189(+), 5-193, 5-202, 5-205, 5-209, 5-210, 5-212, 5-214˜5-216, 5-219, 5-219(+), 5-220˜5-223, 5-226, 5-228, 5-230, 5-231, 5-233, 5-234, 5-236, 5-238, 5-240, 5-242, 5-243*, 5-245˜5-247, 5-251, 5-254, 5-256, 5-258*, 5-259, 5-261, 5-264, 5-272˜5-275, 5-277˜5-280, 5-282, 5-284˜5-288, 5-291, 5-294, 5-295, 5-300, 5-301, 5-306, 5-307, 5-309, 5-310*, 5-313˜5-315, 5-320, 5-321, 5-323, 5-330, 5-334, 5-335, 5-339, 5-341, 5-343, 5-344, 5-348, 5-352, 5-353˜5-358, 5-359*, 5-360, 5-362, 5-364, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-383, 5-384, 5-385*, 5-387, 5-389, 5-390, 5-392, 5-393, 5-398, 5-399, 5-401, 5-409, 5-410, 5-415, 5-418, 5-421˜5-424, 5-427, 5-428, 5-433, 5-434, 5-440˜5-442, 5-446, 5-453, 5-455, 5-458˜5-465, 5-468, 5-470˜5-484, 5-486, 5-487, 5-490, 5-491, 5-494˜5-499, 5-510, 5-512, 5-515, 5-516, 5-519, 5-523, 5-527˜5-529, 5-532, 5-538, 5-541, 5-541(S), 5-546, 5-551˜5-554, 5-557, 5-558, 5-560, 5-569˜5-576, 5-581, 5-583, 5-587, 5-588, 5-608, 5-611, 5-612, 5-617, 5-619, 5-628, 5-630˜5-632, 5-637, 5-638, 5-642, 5-644, 5-646, 5-654, 5-655, 5-662, 5-664, 5-669, 5-670, 5-672, 5-674, 5-684, 5-686, 6-001, 6-003, 6-005*, 6-007, 6-009˜6-012, 6-015*, 6-016˜6-021, 6-022*, 6-027, 6-028, 6-030˜6-033, 6-035˜6-044, 6-048˜6-050, 6-054, 6-056˜6-059, 6-063, 6-066, 6-074˜6-076, 6-078˜6-084, 6-086, 6-089˜6-095, 6-097, 6-098, 6-100˜6-103, 6-112, 6-114, 6-115, 6-121, 6-124, 6-130˜6-132, 7-003˜7-007, 7-009, 8-005, 8-006, 9-004, 9-009, 10-002, 10-006, 11-005, 11-006, 11-026, 11-118, 11-125, 11-130, 12-004. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 13 Insecticidal Test Against Japanese Mealybug

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid theron, and 10-Japanese mealybug (Planococcus kraunhiae) in the first instar larva per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-011, 1-177, 1-182, 2-020, 2-028, 2-029*, 2-033, 2-034*, 2-035*, 2-037*, 2-039*, 2-040*, 2-041*, 2-042*, 2-044*, 2-045*, 2-046*, 2-047, 2-048*, 2-049*, 2-050˜2-052, 2-055*, 2-057, 2-059, 2-062, 2-065˜2-067, 3-065, 3-069, 3-085, 3-086, 3-091˜3-093, 3-104, 3-109, 3-125, 3-151, 4-003, 4-004, 4-006, 5-001, 5-003, 5-005, 5-007, 5-009, 5-013˜5-015, 5-017, 5-022, 5-023, 5-029, 5-037, 5-039˜5-041, 5-045˜5-050, 5-052, 5-053, 5-057˜5-061, 5-063˜5-065, 5-067˜5-075, 5-075(+), 5-076˜5-078, 5-081, 5-083˜5-089, 5-090*, 5-091˜5-094, 5-098˜5-105, 5-109, 5-111˜5-114, 5-116˜5-118, 5-121, 5-123, 5-126, 5-128, 5-129*, 5-130, 5-131*, 5-138˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158˜5-160, 5-161*, 5-162, 5-164, 5-165, 5-166, 5-167*, 5-168*, 5-171, 5-172*, 5-179˜5-188, 5-189(+), 5-190(+), 5-192˜5-194, 5-201, 5-202, 5-205, 5-206, 5-208*, 5-210˜5-212, 5-214˜5-216, 5-219, 5-219(+), 5-221, 5-222, 5-223, 5-226˜5-234, 5-236˜5-240, 5-242, 5-245˜5-247, 5-249, 5-251, 5-253, 5-254, 5-255*, 5-256, 5-257, 5-258*, 5-259, 5-261, 5-264, 5-269*, 5-271*, 5-272˜5-288, 5-291, 5-292, 5-295˜5-297, 5-299˜5-301, 5-302*, 5-303, 5-306, 5-307, 5-309, 5-310*, 5-312˜5-315, 5-318, 5-319, 5-321, 5-322, 5-323, 5-331, 5-332, 5-334˜5-336, 5-338, 5-339, 5-344, 5-345, 5-348, 5-349, 5-353˜5-358, 5-360˜5-362, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387, 5-388, 5-390, 5-392, 5-393, 5-395, 5-396*, 5-397˜5-399, 5-401, 5-406, 5-407, 5-410, 5-412, 5-417˜5-419, 5-422˜5-424, 5-426˜5-434, 5-439˜5-443, 5-445, 5-446, 5-452, 5-453, 5-457, 5-458, 5-460, 5-461, 5-463˜5-465, 5-468, 5-470˜5-473, 5-475˜5-477, 5-480, 5-482˜5-485, 5-487, 5-488, 5-490˜5-492, 5-494˜5-496, 5-498, 5-500, 5-516, 5-519, 5-521˜5-523, 5-525, 5-527, 5-531, 5-532, 5-538, 5-541, 5-543, 5-546, 5-547, 5-549˜5-554, 5-558, 5-569, 5-572˜5-576, 5-579, 5-581˜5-584, 5-587, 5-589, 5-599, 5-605, 5-607, 5-616, 5-623, 5-627, 5-628, 5-637, 5-638, 5-647, 5-651, 5-654˜5-656, 5-658˜5-662, 5-664˜5-666, 5-668˜5-672, 5-674, 5-684˜5-686, 6-001˜6-003, 6-005*, 6-006*, 6-007˜6-013, 6-015*, 6-016˜6-021, 6-022*, 6-023, 6-024*, 6-025*, 6-026˜6-050, 6-054˜6-056, 6-058, 6-059, 6-063, 6-066, 6-074˜6-076, 6-078˜6-080, 6-080(+), 6-082˜6-085, 6-089, 6-090˜6-096, 6-098˜6-102, 6-103, 6-110, 6-114, 6-115, 6-130˜6-132, 7-003˜7-010, 8-003, 9-003, 9-011, 10-002, 10-006, 11-024˜11-026, 11-043, 11-045, 11-056, 11-058, 11-059, 11-089, 11-120, 11-125, 11-132, 12-006, 12-008. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 14 Insecticidal Test Against Cucurbit Leaf Beetle

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of cucumber for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-cucurbit leaf beetle (Aulacophora femoralis) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-005, 1-015, 1-016, 1-040, 1-042, 1-055˜1-057, 1-059, 1-061˜1-067, 1-069˜1-071, 1-073, 1-074, 1-076, 1-077, 1-079˜1-081, 1-083˜1-085, 1-087, 1-088, 1-090, 1-092˜1-095, 1-098, 1-099, 1-102, 1-104˜1-110, 1-113, 1-116, 1-118, 1-119, 1-122˜1-129, 1-131, 1-135, 1-136, 1-138, 1-146, 1-147, 1-151˜1-153, 1-155˜1-157, 1-159, 1-166, 1-167, 1-171, 1-172, 1-174˜1-177, 1-179˜1-185, 1-187˜1-189, 1-194, 1-199, 1-206, 1-207, 1-210, 1-212, 1-214, 1-215, 1-220, 1-225, 2-001, 2-004, 2-006, 2-011, 2-013, 2-019˜2-022, 2-025˜2-029, 2-031, 2-032, 2-034˜2-055, 2-057˜2-068, 3-002, 3-003, 3-006, 3-011, 3-018, 3-025˜3-028, 3-031˜3-035, 3-037, 3-044, 3-046, 3-047, 3-050, 3-058, 3-061˜3-065, 3-068˜3-072, 3-074, 3-076, 3-078˜3-081, 3-084˜3-087, 3-089˜3-095, 3-097˜3-116, 3-118˜3-125, 3-127˜3-132, 3-134˜3-136, 3-138˜3-143, 3-145˜3-151, 4-003˜4-007, 4-009˜4-011, 5-001˜5-015, 5-017, 5-021˜5-023, 5-028˜5-042, 5-044˜5-075, 5-075(+), 5-075(−), 5-076˜5-081, 5-083˜5-095, 5-097, 5-099˜5-107, 5-109˜5-130, 5-132˜5-135, 5-137˜5-151, 5-151(+), 5-151(−), 5-152˜5-156, 5-158˜5-189, 5-189(+), 5-190(+), 5-191˜5-219, 5-219(+), 5-219(−), 5-220˜5-236, 5-238˜5-296, 5-298˜5-326, 5-329˜5-339, 5-341˜5-350, 5-352˜5-363, 5-365, 5-369, 5-371, 5-374˜5-403, 5-405˜5-413, 5-415˜5-447, 5-449, 5-452˜5-455, 5-458˜5-491, 5-493˜5-503, 5-505, 5-507˜5-534, 5-536˜5-540, 5-540(+), 5-541, 5-541(R), 5-541(S), 5-542˜5-560, 5-562˜5-570, 5-572˜5-590, 5-592˜5-602, 5-604˜5-609, 5-611˜5-619, 5-621˜5-648, 5-650, 5-651, 5-653˜5-672, 5-674, 5-676, 5-678, 5-684˜5-686, 6-001˜6-013, 6-015˜6-024, 6-026˜6-051, 6-053˜6-067, 6-070, 6-071, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-086, 6-089˜6-096, 6-098˜6-106, 6-108˜6-115, 6-117˜6-127, 6-129˜6-133, 7-001˜7-010, 8-001˜8-007, 9-003, 9-009, 9-010, 10-002˜10-005, 11-005, 11-015, 11-017, 11-020, 11-023˜11-026, 11-038, 11-043, 11-045, 11-046, 11-052˜11-054, 11-056˜11-060, 11-066, 11-067, 11-072, 11-076, 11-098, 11-099, 11-101˜11-104, 11-106, 11-108, 11-110, 11-112˜11-114, 11-119, 11-120, 11-124, 11-125, 11-129, 11-130, 11-132, 12-006.

Test Example 15 Insecticidal Test Against Serpentine Leaf Miner

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of common bean on which serpentine leaf miner (Liriomyza trifolii) laid eggs (10 eggs/leaf) for about 10 seconds, and after air-drying, they were placed on a wet filter paper laid in a styrol cup having an inner diameter of 7 cm, and the styrol cup was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-175, 1-177, 2-029*, 2-034*, 2-035*, 2-044*, 2-045*, 2-050, 2-051, 2-057, 2-059, 2-062, 2-064, 2-065, 2-067, 3-060, 3-068, 3-069, 3-071, 3-072*, 3-085, 3-086, 3-093, 3-105, 3-109, 3-112, 3-125, 3-148, 3-151, 5-001, 5-003, 5-005, 5-007, 5-009, 5-015, 5-022, 5-023, 5-036, 5-037, 5-040, 5-041, 5-045˜5-053, 5-058˜5-061, 5-063˜5-065, 5-067, 5-068, 5-070˜5-075, 5-075(+), 5-076, 5-077, 5-081, 5-083, 5-085˜5-089, 5-090*, 5-091˜5-094, 5-099˜5-105, 5-113, 5-117˜5-119, 5-120*, 5-121˜5-123, 5-124*, 5-126, 5-129*, 5-131*, 5-133*, 5-138˜5-142, 5-144, 5-145, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-154, 5-156, 5-158, 5-160, 5-161*, 5-162, 5-164˜5-166, 5-168*, 5-169, 5-171, 5-172*, 5-178, 5-180, 5-182˜5-188, 5-189(+), 5-201, 5-202, 5-208*, 5-209, 5-210, 5-212, 5-214˜5-216, 5-217*, 5-219, 5-219(+), 5-221˜5-223, 5-226˜5-234, 5-236, 5-238, 5-239, 5-241, 5-245˜5-247, 5-251, 5-256, 5-257, 5-258*, 5-259, 5-261, 5-264, 5-265, 5-270, 5-274, 5-275, 5-283, 5-284, 5-286, 5-291, 5-294, 5-295, 5-302*, 5-303, 5-306, 5-309, 5-310*, 5-313˜5-315, 5-319, 5-323, 5-335, 5-336, 5-338, 5-339, 5-341, 5-344, 5-345, 5-353˜5-358, 5-360, 5-362, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387, 5-388, 5-390, 5-392, 5-393, 5-395, 5-396*, 5-397˜5-401, 5-408˜5-413, 5-415, 5-417˜5-423, 5-425˜5-430, 5-432, 5-433, 5-439˜5-441, 5-443, 5-445, 5-446, 5-452, 5-453, 5-455, 5-458˜5-465, 5-467, 5-468, 5-470˜5-488, 5-490, 5-491, 5-494˜5-499, 5-501, 5-508˜5-512, 5-515˜5-517, 5-519, 5-520˜5-523, 5-527˜5-532, 5-538, 5-539, 5-541, 5-541(S), 5-543, 5-549, 5-551˜5-554, 5-556˜5-560, 5-566, 5-569, 5-570, 5-572˜5-576, 5-579, 5-581, 5-584, 5-596, 5-601, 5-606, 5-616, 5-617, 5-630, 5-631, 5-634, 5-635, 5-637, 5-638, 5-642, 5-643, 5-646, 5-651, 5-653˜5-657, 5-659, 5-660, 5-662, 5-664˜5-672, 5-674, 5-684˜5-686, 6-001, 6-004*, 6-005*, 6-006*, 6-007, 6-008, 6-011˜6-013, 6-015*, 6-016˜6-021, 6-022*, 6-024*, 6-025*, 6-027, 6-031, 6-033˜6-041, 6-043, 6-044, 6-048˜6-050, 6-054˜6-056, 6-066, 6-070, 6-074˜6-076, 6-078, 6-079, 6-081, 6-083, 6-085, 6-089, 6-091, 6-092, 6-093, 6-095, 6-098, 6-100, 6-102, 6-103, 6-110, 6-114, 6-123, 6-124, 6-129˜6-133, 7-003, 7-005˜7-009. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 16 Insecticidal Test Against Two-Spotted Spider Mite

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10 larvae of two-spotted spider mite (Tetranychus urticae) per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-177, 1-182, 2-027, 2-028*, 2-029*, 2-034*, 2-035*, 2-036, 2-037*, 2-039*, 2-040*, 2-041*, 2-042*, 2-044*, 2-045*, 2-046*, 2-047, 2-048*, 2-049*, 2-050˜2-052, 2-057˜2-063, 2-065˜2-067, 3-068, 3-084, 3-086, 3-109, 3-110, 3-1,2,3-114, 3-124, 3-131, 3-151, 5-001, 5-003, 5-005, 5-007˜5-009, 5-011, 5-013, 5-015, 5-019, 5-021, 5-022, 5-023, 5-028, 5-029, 5-035˜5-037, 5-040, 5-041, 5-045˜5-053, 5-057˜5-075, 5-075(+), 5-076˜5-078, 5-080˜5-089, 5-090*, 5-091˜5-094, 5-098˜5-105, 5-109, 5-112˜5-114, 5-117˜5-119, 5-121˜5-123, 5-126, 5-128, 5-129*, 5-130, 5-132, 5-134, 5-136˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-152, 5-153*, 5-154˜5-156, 5-158˜5-160, 5-161*, 5-162˜5-166, 5-167*, 5-168*, 5-171, 5-172*, 5-177˜5-180, 5-182˜5-188, 5-189*, 5-189(+), 5-190(+), 5-191, 5-192, 5-196*, 5-197*, 5-199˜5-202, 5-204˜5-207, 5-208*, 5-209˜5-212, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-219(−), 5-220˜5-234, 5-235*, 5-236, 5-238˜5-242, 5-243*, 5-245˜5-247, 5-249, 5-251, 5-254, 5-255*, 5-256, 5-257, 5-258*, 5-259, 5-261, 5-264, 5-265, 5-269*, 5-271*, 5-273˜5-275, 5-277˜5-279, 5-283˜5-286, 5-288, 5-291, 5-292, 5-294, 5-295, 5-299˜5-301, 5-306, 5-307, 5-312˜5-316, 5-321, 5-323, 5-325, 5-330, 5-336, 5-338, 5-339, 5-341, 5-344, 5-345, 5-349, 5-353˜5-358, 5-360, 5-362, 5-374, 5-375, 5-376*, 5-377*, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-386*, 5-387˜5-395, 5-396*, 5-397˜5-399, 5-401, 5-402, 5-405, 5-406, 5-408˜5-413, 5-415, 5-417˜5-419, 5-421˜5-423, 5-425˜5-427, 5-430, 5-432, 5-433, 5-440, 5-441, 5-443, 5-445, 5-452˜5-455, 5-457˜5-463, 5-465, 5-467, 5-468, 5-470˜5-487, 5-489˜5-492, 5-494˜5-499, 5-503, 5-505, 5-506, 5-509˜5-513, 5-515˜5-525, 5-527˜5-534, 5-538, 5-539, 5-540(+), 5-543˜5-545, 5-548˜5-554, 5-557˜5-560, 5-566, 5-568˜5-570, 5-572˜5-576, 5-578, 5-579, 5-581, 5-583, 5-584, 5-600, 5-601, 5-604, 5-606, 5-616, 5-617, 5-630, 5-631, 5-635, 5-637, 5-638, 5-642, 5-646, 5-647, 5-650, 5-651, 5-654˜5-657, 5-659˜5-662, 5-664˜5-672, 5-678, 5-684˜5-686, 6-001, 6-003, 6-007, 6-008, 6-011˜6-013, 6-015*, 6-016˜6-021, 6-023, 6-027, 6-030˜6-044, 6-046˜6-050, 6-054˜6-056, 6-066, 6-074˜6-076, 6-078, 6-079, 6-082˜6-085, 6-089˜6-093, 6-095, 6-096, 6-098, 6-100, 6-102, 6-103, 6-110, 6-112, 6-114, 6-115, 6-121, 6-123, 6-124, 6-129˜6-133, 7-003˜7-010, 8-003, 10-002, 10-006, 11-026, 11-098, 11-108, 12-002. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.

Test Example 17 Insecticidal Test Against Pink Citrus Rust Mite

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a mandarin orange cut out so as to have the same diameter was laid thereon, and 10 larvae of pink citrus rust mite (Aculops pelekassi) per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 1-177, 3-093, 3-112, 5-001˜5-003, 5-005, 5-008, 5-009, 5-022, 5-023, 5-036, 5-037, 5-040, 5-041, 5-046, 5-047, 5-049, 5-050, 5-053, 5-057˜5-059, 5-061, 5-063, 5-065, 5-066, 5-069˜5-071, 5-074˜5-077, 5-081, 5-083, 5-084, 5-086, 5-088, 5-111˜5-113, 5-121, 5-137˜5-140, 5-148, 5-151, 5-174, 5-182, 5-183, 5-185, 5-187, 5-188, 5-202, 5-205, 5-206, 5-215, 5-216, 5-219˜5-221, 5-225, 5-226, 5-233˜5-235, 5-241, 5-247, 5-274, 5-285, 5-291, 5-294, 5-295, 5-301, 5-313, 5-323, 5-331, 5-334, 5-338, 5-339, 5-355, 5-360, 5-374, 5-378, 5-387˜5-390, 5-393, 5-397, 5-398, 5-480, 5-494, 5-638, 5-642, 5-645, 6-003, 6-017, 6-020, 6-021, 6-027, 6-031, 6-033˜6-035, 6-043, 6-049, 6-054, 6-064, 6-070, 6-076, 6-131, 7-003, 7-007˜7-009, 10-002.

Test Example 18 Insecticidal Test Against Broad Mite

A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10 adults of broad mite (Polyphagotarsonemus latus) per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 3-093, 5-009, 5-036, 5-037, 5-040, 5-041, 5-050, 5-053, 5-058, 5-063, 5-067, 5-071, 5-075˜5-077, 5-083, 5-088, 5-089, 5-113, 5-121, 5-140, 5-147, 5-148, 5-151, 5-174, 5-179, 5-185, 5-188, 5-214, 5-215, 5-219, 5-230, 5-233˜5-236, 5-249, 5-251, 5-254, 5-274, 5-288, 5-289, 5-291, 5-294, 5-309, 5-332, 5-339, 5-355, 5-360, 5-374, 5-375, 5-387, 5-398, 5-474, 5-476, 5-480, 5-494, 5-604, 5-642, 6-017, 6-026, 6-031, 6-033˜6-035, 6-038, 6-045, 6-064, 6-070, 6-076, 6-131, 7-003, 7-007˜7-009.

Test Example 19 Insecticidal Test Against Ctenocephalides felis

After 400 μl of acetone solution in which 4 mg of the compound of the present invention was dissolved in 40 ml of acetone (concentration 100 ppm) was coated on the bottom face and side face of a laboratory dish having an inner diameter of 5.3 cm, acetone was vaporized to prepare a thin film of the compound of the present invention on the inner wall of the laboratory dish. As the surface area of the inner wall is 40 cm², the treated dosage is 1 μg/cm². 10 adults of Ctenocephalides felis (male and female are mixed) were left in the laboratory dish, covered with lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 4 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with one district.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 2-029*, 2-052, 3-151, 5-002, 5-003, 5-005, 5-007, 5-008, 5-012, 5-013, 5-023, 5-029, 5-037, 5-058, 5-071*, 5-072, 5-075*, 5-076, 5-077, 5-086, 5-088*, 5-093, 5-100*, 5-101*, 5-111*, 5-117, 5-121, 5-130*, 5-138, 5-139, 5-140*, 5-142*, 5-148*, 5-151*, 5-160*, 5-161*, 5-165*, 5-174*, 5-182*, 5-184, 5-187, 5-188, 5-192, 5-205, 5-206, 5-209, 5-214*, 5-215*, 5-218, 5-219*, 5-223, 5-229, 5-230, 5-232, 5-234*, 5-235*, 5-236, 5-238, 5-240, 5-241*, 5-243*, 5-245*, 5-247, 5-264, 5-274*, 5-287, 5-291, 5-294, 5-310*, 5-312, 5-313, 5-323, 5-354*, 5-356*, 5-359*, 5-360, 5-362, 5-376*, 5-377*, 5-378*, 5-379*, 5-383*, 5-384*, 5-387*, 5-389*, 5-390, 5-393, 5-399*, 5-401, 5-405*, 5-412*, 5-423*, 5-427*, 5-429*, 5-430*, 5-440*, 5-461*, 5-466*, 5-468*, 5-470*, 5-473, 5-474*, 5-475, 5-476, 5-477*, 5-478*, 5-480*, 5-487, 5-494*, 5-495˜5-499, 5-579*, 5-587*, 5-623, 5-646*, 5-648*, 5-658, 6-020, 6-026, 6-033, 6-034, 6-035*, 6-043*, 6-046˜6-049, 6-054, 6-055, 6-064, 6-065*, 6-074, 6-092, 6-094, 6-095, 6-129, 6-130, 6-133, 7-002*, 7-004, 7-008*, 7-009. In the interim, the indication of “*” shows that the insecticidal test was carried out with a treated dosage of 0.1 μg/cm².

Test Example 20 Insecticidal Test Against American Dog Tick

After 400 μl of acetone solution in which 4 mg of the compound of the present invention was dissolved in 40 ml of acetone (concentration 100 ppm) was coated on the bottom face and side face of two laboratory dishes having an inner diameter of 5.3 cm, acetone was vaporized to prepare a thin film of the compound of the present invention on the inner wall of the laboratory dish. As the surface area of the inner wall is 40 cm², the treated dosage is 1 μg/cm². 10-American dog tick (Dermacentor variabilis) (male and female are mixed) in the stage of protonymph were left in the laboratory dishes, two laboratory dishes together were sealed with a tape so that ticks do not escape, and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 4 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with one district.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 2-029*, 2-052, 2-054*, 5-003, 5-005, 5-008, 5-023, 5-029, 5-037, 5-058, 5-063*, 5-071*, 5-072, 5-075*, 5-076*, 5-077, 5-086, 5-088*, 5-093*, 5-100*, 5-101*, 5-117, 5-121, 5-128, 5-130*, 5-138, 5-139, 5-140*, 5-142*, 5-148*, 5-151, 5-160*, 5-161*, 5-165*, 5-174*, 5-182*, 5-184, 5-187, 5-188, 5-191, 5-192, 5-205, 5-206, 5-209, 5-214*, 5-215*, 5-219*, 5-223, 5-229, 5-230, 5-232, 5-233*, 5-234*, 5-235*, 5-236, 5-238, 5-240, 5-241*, 5-243*, 5-245*, 5-247, 5-264, 5-274*, 5-287, 5-291, 5-294, 5-308*, 5-309*, 5-310*, 5-312, 5-313, 5-320, 5-321, 5-323, 5-354*, 5-356*, 5-359*, 5-360, 5-362, 5-376*, 5-377*, 5-378*, 5-379*, 5-383*, 5-384*, 5-386*, 5-387*, 5-390, 5-393, 5-399*, 5-401*, 5-405*, 5-412*, 5-418*, 5-423*, 5-427*, 5-429*, 5-430*, 5-432*, 5-440*, 5-461*, 5-466*, 5-468*, 5-469*, 5-470*, 5-473*, 5-474*, 5-475*, 5-476*, 5-477*, 5-478*, 5-480*, 5-487*, 5-494*, 5-495*, 5-496*, 5-497*, 5-498*, 5-499*, 5-500*, 5-555*, 5-579*, 5-581*, 5-585*, 5-587*, 5-588*, 5-589*, 5-593*, 5-601*, 5-607*, 5-610*, 5-623*, 5-638*, 5-646*, 5-648*, 5-654*, 5-658*, 6-020, 6-026, 6-033, 6-034*, 6-035*, 6-043*, 6-046˜6-049, 6-054, 6-055, 6-064, 6-065*, 6-074, 6-092*, 6-094*, 6-095*, 6-129*, 6-130*, 6-133*, 7-004, 7-008*, 7-009, 11-056. In the interim, the indication of “*” shows that the insecticidal test was carried out with a treated dosage of 0.1 μg/cm².

Test Example 21 Insecticidal Test Against German Cockroach

A chemical solution having a concentration of 10 μg/μl was prepared by diluting the compound of the present invention with acetone. The chemical solution was coated on the abdominal region of male adults of German cockroach (Blattella germanica) in an amount of 1 μl per cockroach, and the treated cockroaches were contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with five districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 5-075, 5-140*, 5-147*, 5-148*, 5-151*, 5-174*, 5-234*, 5-412*, 5-480*, 5-494*, 5-541, 5-638*, 6-103*.

Test Example 22 Insecticidal Test Against Musca domestica

A chemical solution having a concentration of 1 μg/μl was prepared by diluting the compound of the present invention with acetone. The chemical solution was coated on the abdominal region of female adults of Musca domestica in an amount of 1 μl per fly, and the treated flies were contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with ten districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention:

No. 5-075, 5-140, 5-147, 5-148, 5-151, 5-174, 5-219, 5-234, 5-412, 5-480, 5-494, 5-541, 5-638, 6-103. Test Example 23 Insecticidal Test Against Eastern Subterranean Termite

A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 10 ppm. 0.5 ml of the chemical solution was added dropwise in 10 g of sand and mixed. A filter paper and the sand treated with the chemical solution were placed in a laboratory dish in which 1% agar was laid. 10-Eastern subterranean termite (Reticulitermes flavipes) per dish was left and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 5-234.

Test Example 24 Insecticidal Test Against Rust-Red Flour Beetle

A chemical solution having a concentration of 0.1 mg/ml was prepared by diluting the compound of the present invention with acetone. After 10 ml of the chemical solution was added dropwise in 10 g of bran, 20 adults of rust-red flour beetle (Tribolium castaneum) were left therein, and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 months was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested. The compounds of the present invention: No. 5-234.

INDUSTRIAL APPLICABILITY

The isoxazoline-substituted benzanilide compounds according to the present invention are extremely useful compounds showing an excellent pesticidal activity, particularly an insecticidal and acaricidal activity, and causing little adverse effect against non-targeted beings such as mammals, fishes and useful insects.

LENGTHY TABLES The patent application contains a lengthy table section. A copy of the table is available in electronic form from the USPTO web site (http://seqdata.uspto.gov/?pageRequest=docDetail&DocID=US20090312330A1). An electronic copy of the table will also be available from the USPTO upon request and payment of the fee set forth in 37 CFR 1.19(b)(3). 

1. An endo- or ecto-parasiticide for mammals or birds containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound, an optically active form or the salt thereof according to a formula

wherein (X)_(m) is 3,5-Cl₂, 3-Br, 3-I, 4-I, 3-CF₃, 3-OCF₃, 3-SCF₃, 3,5-F₂, 3,5-Br₂, 3,5-(CF₃)₂, 3-CF₃-5-OCH₃, 3,4-C₁₂ or 3,5-C1₂-4-CH₃, Y is H, CH₃, Br, CH₂CH₃, SCH₃, Cl or I, R^(I) is CH(CH₃)CH₂OCH₃, NH(4-cyanophenyl), 2-tetrahydrofuryl, CH₂CF₃, CH₂ (2-pyridyl), CH₂CH₂(2-pyridyl), cyclobutyl, CH₂(cyclobutyl), CH₂CH₂CH₂OCH₃, CH₂CH₂OCH₂CH₃, tetrahydrofurfuryl, CH₂(1,3-dioxolan-2-yl), CH₂CH₂SCH₂CH₃, CH₂CH(CH₃)S(O)CH₃, CH₂CH(CH₃)SO₂CH₃, CH₂C(O)CH₃, CH₂C(CH₃)═NOCH₃, CH(phenyl)CN, CH(CH₃)C(O)OCH₃, CH₂C(O)NHCH₃, CH₂C(O)N(CH₃)₂, CH₂C(O)NHCH₂CH₃, CH₂C(O)NHPr-i, CH₂C(O)NHCH₂CH₂Cl, CH₂C(O)NHCH₂CF₃, CH₂C(O)NHCH₂CH═H₂, CH₂C(O)N(CH₃)CH₂CH═CH₂, CH₂C(O)NHCH₂C≡CH, CH(CH₃)C(O)NHCH₂CH₂Cl, CH₂CH═CH₂, CH₂CH═CC1₂, benzyl, CH(CH₃)(phenyl), C(CH₃)₂(phenyl), CH₂(2-furyl), CH₂(2-thienyl), CH₂(3-chloro-5-isoxazolyl), CH₂(1-methylpyrazol-5-yl), CH₂(3-chloro-1-methylpyrazol-5-yl), CH₂(4-trifluoromethylthiazol-2-yl), CH₂(4-thiazolyl), CH₂(2-chlorothiazol-5-yl), CH₂(1,2,4-oxadiazol-5-yl), CH₂(1,3,4-oxadiazol-5-yl), CH₂(1,3,4-thiadiazol-5-yl]), CH₂(2-pyridyl), CH(CH₃)(2-pyridyl), CH₂(4-chloropyridin-2-yl), CH₂(6-chloropyridin-2-yl), CH₂(3-pyridyl), CH₂(2-chloropyridin-5-yl), CH₂(2-pyrimidyl), CH₂(4-pyrimidyl), CH₂(2-methylpyrazin-5-yl), NHC(O)OCH₂CH₃, N(CH₃)(phenyl), NH(3-chloropyridin-2-yl), NH(2-pyrimidyl), N(CH₃)(2-pyrimidyl), 4-pyrimidyl, CH₂CH₂OCH₃, CH₂C(O)NHCH₂CH₂Cl, CH₂C(O)NHCH₂CF₃, CH₂CH₂CF₃, CH(CF₃)OCH₃, N—(CH₂CF₃)-pyrrolidone-3-yl, CH(CH₃)C(O)NHCH₂CF₃, CH(CH₃)(2-thiazolyl), CH(CF₃)(1H-1,2,4-triazol-1-yl), C(O)NHCH₂CF₃, C(S)NHCH₂CF₃, 1-methylpyrazol-3-yl, 4-chloropyrimidin-2-yl, CH₂OCH₃, CH₂OCH₂CH₃, CH₂OCH₂CH₂CH₃, CH₂OCH(CH₃)₂, CH₂OCH₂CH₂Cl, CH₂OCH₂CHF₂ CH₂OCH₂CF₃, CH(CH₃)OH, 3-tetrahydrofuryl (R), 2-tetrahydropyranyl, CH₂SCH₃, CH₂S(O)CH₃CH₂SO₂CH₃, C(O)NHCH₂CH═CH₂, 3-fluorophenyl, 5-chlorothiazol-2-yl, 6-methoxy-2-tetrahydropyranyl, CH₂(4-pyridyl), N(CH₃)phenyl or tetrahydrothiophene-2-yl, R² is H, CH₃, CH₂CF₃, CH₂C≡CH, C(O)CH₃, C(O)CH₂CH₃, C(O)OCH₃, C(O)OBu-i, C(O)OCH₂CH₂C1, C(O)OCH₂CH₂OCH₃, C(O)OCH₂CH═CH₂, CH₂CH₃, cyclopropyl, CH₂OCH₂CH₃, CH₂OCH₃, and R³ is CF₃, CHF₂, CF₂C1 or CF₂CF₃.
 2. The endo- or ecto-parasiticide for mammals or birds of claim 1 wherein the active ingredient is 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl)benzamide, an optically active form, or a salt thereof.
 3. A method for controlling endo- or ecto-parasites of mammals or birds comprising administration of an effective amount of the endo- or ecto-parasiticide of claim
 1. 4. The method of claim 3 wherein said administration is oral administration.
 5. The method of claim 3 wherein said administration is parenteral administration.
 6. The method of claim 3 wherein said administration is injection.
 7. The method of claim 3 wherein said administration is intramuscular, subcutaneous, intravenous or intraperitoneal injection.
 8. The method of claim 3 wherein said administration is transdermal administration.
 9. The method of claim 3 wherein said administration is transnasal administration.
 10. The method of claim 3 wherein said administration is dipping, spray, bathing, washing, pouring-on, spotting-on or dusting.
 11. A method for controlling endo- or ecto-parasites of mammals or birds comprising administration of an effective amount of the endo- or ecto-parasiticide of claim
 2. 12. The method of claim 11 wherein said administration is oral administration.
 13. The method of claim 11 wherein said administration is parenteral administration.
 14. The method of claim 11 wherein said administration is injection.
 15. The method of claim 11 wherein said administration is intramuscular, subcutaneous, intravenous or intraperitoneal injection.
 16. The method of claim 11 wherein said administration is transdermal administration.
 17. The method of claim 11 wherein said administration is transnasal administration.
 18. The method of claim 11 wherein said administration is dipping, spray, bathing, washing, pouring-on, spotting-on or dusting. 